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Love this question and your great supporting the habbit 😛  Its a great hobby and would recommend it to anyone. Some of my best friends I met riding.

Conventional wisdom shared thus far makes sense and great basis, especially any classes where they provide a loaner. I believe one of the biggest factors really boils down to maturity level and if you both agree on where that is at.

Do you think he has a good head on his shoulders, decent impulse control, and will keep his wits about him?  Since he had some practical experience, did he show good confidence and comfort level?  Those bits can help point toward the range of bike that could work and keep him engaged for a longer period of time.  If the answers to those are positive, you may consider something in the intermediate weight class. Inline 4 600's to 750's. 250 to 500 parallel twins are great to point, but tend to be outgrown the quickest. Especially if he gets some riding buddies and they swap bikes.

How is the market? I have to think today's market may be similar to used cars where things are overpriced or limited offerings. I just scanned thru Nashville Craigslist and it was slim pickens.  I can see how that would make new a more viable option, but depending on how engaged he is and how good that first choice is, that may make the least financial sense even if those same used are asking close to that price.  What I've observed with used beginner bikes or those owned by younger people is they tend to lack real life experience in selling so tend to overprice them, which is why their adds are there (well priced things are gone and you dont see em). Wait em out if you must.

But iff he gets bitten by the bug, I'd agree with your early thought that he would get disinterested fast. Your gonna take a good hit on anything new since you cant rely on used overpriced values that dont move.  Your budget may be in line with better value and offerings in something a bit larger if (after consideration) factors point to that being a viable option. Bringing me back to intermediate weight class. YZF600 (R6S), 750 something, 900 standard (naked detuned sporty bike).

The other thing I use to tell first time buyers if they like the look of fully faired sportbikes, is that gravity can win a stop light balancing contest, or remind you if you dont set a kickstand right. Seems 90%+ of first time owners will drop their bike and fairings are expensive. Naked bikes are 90% the fun without that spendy bodywork. Extra points of naked bikes.

FWIW, I got bitten by the bug in 1987 when I bought my first bike, a Ninja 750. It and I both survived. I sold it in perfect shape 2 years later when I moved up to a GSXR-1100.  I've never been without at least one since then.

Good luck, and let us know what you guys do. 

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Best advice I ever got was:

"Ride as though everyone else on the road is trying to kill you!"

I started on a Honda XL250 dual sport at 18.  Great bike for tooling around town and in the country.  That was when we had that stupid nationwide 55mph speed limit.  That's about all the little Honda could manage.

Graduated to a Yamaha XT650.  Big thumper could idle up most hills it had so much torque!  Then a Yamaha 650 twin, Honda VF750 Sabre, then a Honda VF1100 Sabre.  Those Honda V-4s were great bike!  I also had a AMF Harley 883 and Street Glide in the '80's.  The less said about those two, the better.

The Motorcycle Safety course is a great idea for any rider.  And I took it after I'd been riding for 20 years.  I may take it again soon, as it helps reinforce good habits and lets you see any bad ones you may have picked up.

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Thanks for the advice. We picked him up a bike last night. It’s an 06 Suzuki Boulevard S40, which is just a newer Savage 650. The big one cylinder engine is different from what I’m used to. It’s nice, and has 2500 miles on it. I thought $2k was a fair price, considering what I’ve looked at. It’s black and sharp. It has mew brakes, new tires, windshield, saddlebags, sissy bar bag, phone holder, new battery, and a fresh oil change. It also came with a helmet, Clymer manual, factory manual, and two oil filters. It was owned and ridden by an older man who decided to get a bigger bike.

I rode it home; about 70 miles last night. Ran great. I think it’ll do.

Edited by gregintenn
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Those are good bikes. One of my friends bought one to "relearn" on after years off motorcycles, and it served that purpose well.  He still rides it often. 

Back when I was a new rider most of us learned on 250's or 350's. My first bike was a brand new 1975 Yamaha RD350, which was a pretty hot bike for its day. I've had some variant of that bike ever since, including the 1989 Canadian-spec RD-350 that's sitting in my garage right now. Those were great bikes to learn handling and you had to be good with a wrench, too. 

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11 hours ago, Erich said:

Do you think he has a good head on his shoulders, decent impulse control, and will keep his wits about him? 

A very valid point. Common sense and self control are absolute musts on a bike. The daughter of some very good friends married a nice young man in his 20s. He bought a bike and got stupid. Got to showing off and street racing. It ended up costing him a leg. ☹️

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Only suggestion is to NOT do what I did.  I was in Germany and had NEVER ridden a motorcycle in my life. The closest I ever came to riding a motorcycle was listening to Arlo Guthrie singing his song from Alice's Restaurant,  The Motorcycle Song, lol.  Anyway a friend of mine had a big Honda Gold Wing, a big one. and he was selling it!  So i made arrangements to buy it and since we were both on the Police bowling team, we decide dot transfer it at the lanes one evening.  This was in Germany, by the way.  We met and he had it leaning on the kickstand.  He asked me if I remembered how the gears worked, and I had no freaking clue, so I said refresh my memory.  He replied this side pedal 3 up and 2 down or something like that.  I already knew where the brakes, clutch and throttle were, so I pulled the bike up, put it in gear and eased across the parking lot, onto the road leading to off base.  I got on the autobahn and drove it home with no real problems, though it got a little dicey at times.  The Germans made us get a license to drive in Germany plus a special one for motorcycles, but they let the military figure out how to do that, so they required one to successfully complete a Motorcycle Safety Course operated by I think it was the Motorcycle Safety Foundation.  There were three courses (Beginners, Intermediate and advanced), taught by experienced riders offered a few times a year.  As it turns out the Beiginners course wasn't scheduled for a few months, but the Advanced course was offered in a couple weeks.  So I signed up for that one, figuring I had 2 weeks to prepare.  So I rode it back and forth to work every day, about 24 miles i guess, and on the weekends I rode it more.  IAs I rolled into the place where they had it, I was feeling pretty good. I mean, I had 2 weeks experience.  Well there was a lot of classroom time with instruction and testing, which i barely passed, then it was ride time!  They had traffic cones set up in a big parking lot and one had to navigate the course without hitting any traffic cones and not putting one's foot on the ground,, Those two things were automatic failures as was dropping the bike!  When my turn came I was pretty nervous, especially when the instructor asked me why I brought such a big bike to this course.  All the other advanced riders had way smaller motorcycles.  Well I made it, not sure how as i had no clue how to ride and zero experience, lol, but I did it, somehow.  As he signed my license and handed it to me he said, well you passed, barely, but you're not really safe to ride, lol.  PLEASE PRACTICE IN A SAFE PLACE!  Well I took his advice and soon I was able to safely navigate the small roads in the little German villages as well as cruise the autobahn at high speed.  Sorry to steal your thread, but I thought some might appreciate how stupid I was.

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17 minutes ago, Defender said:

Only suggestion is to NOT do what I did.  I was in Germany and had NEVER ridden a motorcycle in my life. The closest I ever came to riding a motorcycle was listening to Arlo Guthrie singing his song from Alice's Restaurant,  The Motorcycle Song, lol.  Anyway a friend of mine had a big Honda Gold Wing, a big one. and he was selling it!  So i made arrangements to buy it and since we were both on the Police bowling team, we decide dot transfer it at the lanes one evening.  This was in Germany, by the way.  We met and he had it leaning on the kickstand.  He asked me if I remembered how the gears worked, and I had no freaking clue, so I said refresh my memory.  He replied this side pedal 3 up and 2 down or something like that.  I already knew where the brakes, clutch and throttle were, so I pulled the bike up, put it in gear and eased across the parking lot, onto the road leading to off base.  I got on the autobahn and drove it home with no real problems, though it got a little dicey at times.  The Germans made us get a license to drive in Germany plus a special one for motorcycles, but they let the military figure out how to do that, so they required one to successfully complete a Motorcycle Safety Course operated by I think it was the Motorcycle Safety Foundation.  There were three courses (Beginners, Intermediate and advanced), taught by experienced riders offered a few times a year.  As it turns out the Beiginners course wasn't scheduled for a few months, but the Advanced course was offered in a couple weeks.  So I signed up for that one, figuring I had 2 weeks to prepare.  So I rode it back and forth to work every day, about 24 miles i guess, and on the weekends I rode it more.  IAs I rolled into the place where they had it, I was feeling pretty good. I mean, I had 2 weeks experience.  Well there was a lot of classroom time with instruction and testing, which i barely passed, then it was ride time!  They had traffic cones set up in a big parking lot and one had to navigate the course without hitting any traffic cones and not putting one's foot on the ground,, Those two things were automatic failures as was dropping the bike!  When my turn came I was pretty nervous, especially when the instructor asked me why I brought such a big bike to this course.  All the other advanced riders had way smaller motorcycles.  Well I made it, not sure how as i had no clue how to ride and zero experience, lol, but I did it, somehow.  As he signed my license and handed it to me he said, well you passed, barely, but you're not really safe to ride, lol.  PLEASE PRACTICE IN A SAFE PLACE!  Well I took his advice and soon I was able to safely navigate the small roads in the little German villages as well as cruise the autobahn at high speed.  Sorry to steal your thread, but I thought some might appreciate how stupid I was.

We all had to learn. Thank God I didn’t start with a Gold Wing!

The natural progression is a bicycle, then a mini bike, then a dirt bike, and finally a street bike. At least that’s how I did it.

Edited by gregintenn
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37 minutes ago, Defender said:

a friend of mine had a big Honda Gold Wing, a big one. and he was selling it! 

So....did it come with a jar of pickles?? 😄

 

40 minutes ago, Defender said:

 they let the military figure out how to do that, so they required one to successfully complete a Motorcycle Safety Course operated by I think it was the Motorcycle Safety Foundation.

Funny related story. They required me to take the MSF advanced course to get a base sticker on my bike. I took it at Mather AFB, which is where they held the Navigator school. There were two Navigators in my class. One drills was an accident avoidance quick turn. They had you roll up on a to a set of lights at 25 or so, and they would turn on either the left or right light at the last second and you were to break right or left depending on the light. The only guy to turn the wrong way was one of the Navigators. The other one dropped his brand new VFR1000 on the rear lock up drill.

Sounds like you did great all things considered. I dont think any rider, in the right place or time (or wrong place?) is immune from at least doing something questionable at some point. 

Only way to know where the limit is is to at least dangle a toe over it. Track time is great for that. But its effect on your street riding has ups and downs.

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4 hours ago, gregintenn said:

Thanks for the advice. We picked him up a bike last night. It’s an 06 Suzuki Boulevard S40, which is just a newer Savage 650. The big one cylinder engine is different from what I’m used to. It’s nice, and has 2500 miles on it. I thought $2k was a fair price, considering what I’ve looked at. It’s black and sharp. It has mew brakes, new tires, windshield, saddlebags, sissy bar bag, phone holder, new battery, and a fresh oil change. It also came with a helmet, Clymer manual, factory manual, and two oil filters. It was owned and ridden by an older man who decided to get a bigger bike.

I rode it home; about 70 miles last night. Ran great. I think it’ll do.

You know what they say...  Pics or it didn't happen.   🙂

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19 hours ago, QuackerSmacker said:

Google this: Honda Rebel 500.  I'm thinking about one of these to replace my BMW R1100RS which is just too much bike for this old guy. 

BTW, it's a 1994 w/ showroom looks and under 15,000 miles if anyone's interested......

I would be except for the two projects in my driveway waiting for my attention. Better if it were an RT (for me)

 

Edited by papa61
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2 hours ago, Erich said:

Greg, how excited was he today, did he ride it yet?

Yeah. When we got back home last night, he rode it around the school parking lot with a big grin on his face. It didn't seem like he had any problem with it.

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2 hours ago, Trekbike said:

You know what they say...  Pics or it didn't happen.   🙂

You are correct, sir!

xgiZsd3.jpg
 

LOL! It looks like somebody put a dirt bike motor on a Sportster.

I was surprised when I saw it had a belt drive and not chain and sprockets.

Edited by gregintenn
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On 7/5/2021 at 3:27 PM, gregintenn said:

I think a Honda 230 xr would be an awesome place to start. I told him he might even want to keep it for trail riding after moving up to a dedicated street machine.

Rarely do I recommend more power for newer riders, but I wouldn't hesitate to recommend a DRZ400 for him considering his height.  They aren't crazy powerful, 38hp stock I believe, but can really be livened up with some inexpensive mods.  I've owned two of the DRZs, an SM model, and a street legal E model.  I've ridden the 230, it was a fun little bike, just a little short on power. 

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2 hours ago, gregintenn said:

You are correct, sir!

xgiZsd3.jpg
 

LOL! It looks like somebody put a dirt bike motor on a Sportster.

I was surprised when I saw it had a belt drive and not chain and sprockets.

congrats! that's a good choice. the big thumper will do well for you I'm sure.

 

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Congrats on the find/purchase.  I've had several Suzuki bikes in the Intruder models, still miss my '04 Intruder 1400.  LOL.  Dependable bikes, and should be a good beginners bike for him.

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