Oh boy, I spent the last 5-7 years away from bicycles on a dual sport 
motorcycle spree. Be careful, it's a slippery slope...

First of all, stay away from anything more than 15-20 or so years old. 
Motorcycles don't age well, and the old twin shock, drum brake bikes just 
sucked.

The bike that fits your requirements most closely is a Kawasaki KLX250S. 
Street legal, decent on road and off. The only downside is that it's slow, 
and a little on the heavy side for real off-road work. Very good on dirt 
roads, and very beginner friendly. 

If you can get a street registration for a real dirt bike in your state 
(many can), then a street-legalized Honda XR250R from 1996-2004 would be 
awesome.

I currently ride a Suzuki DR650. It's heavier and more skewed towards road 
riding, but it's good on dirt roads and easy trails. Highway capable, too. 
Simpler to work on than a lawnmower and they haven't made any changes to 
them since 1996, so used parts availability and aftermarket support is 
awesome.

If you want to buy once and cry once, get a new-ish KTM 500EXC. If I had 
the means, there'd be one in my garage right now.


Other notable machines:

Kawasaki KLR650 - owned one, put 12k miles on it. Terrible on road and off. 
But they have a cult following for some reason?
Yamaha WR250R - owned two. Looks like a real dirt bike, but way too heavy 
and underpowered, IMHO. Very complicated with fuel injection and what not.
Suzuki DRZ400 - top heavy and has a very narrow gear spread, so it's really 
buzzy on the road.
BMW F650 singles - owned the first gen "Funduro". Good bikes, but more 
road-oriented. Expensive to buy, and maintain compared to the Japanese 
brands.
Honda XR650L - taller and more top-heavy than the Suzuki DR650. More 
offroad oriented.

Finally, if you really want to fall down the rabbit hole, check out 
ADVRider.com. See ya over there...

Chris


On Friday, September 29, 2017 at 9:06:22 PM UTC-4, drew wrote:
>
> So a while back, i bought some property in the mountains and it came with 
> 2 dirt bikes. They aren't street legal, or attractive, or very high end. 
> We've spent the last year semi renovating the cabin, clearing the land of 
> years of brush pile up, but we've finally gotten to the point where we are 
> starting to try to go through some of the stuff in the garage. I have no 
> use for 2 non street worthy, ugly yamahas, but after a little research, it 
> looks like i can get about 3500$ for the pair. 
>
> after thinking about it, i think a (single) motorcycle would be useful and 
> fun to have up there. im trying to figure out what that type of thing would 
> be and, since ive never had any interest in motorcycles, the internet info 
> is overwhelming. i know some of you guys ride all types of bikes, so im 
> hoping to get some direction. 
>
> here is what i'm thinking
> -3500$ or less
> -good on roads and dirt roads. not interested in jumps or anything crazy, 
> but it will have to be able to go off pavement comfortably
> -reliable/durable/parts easily found and cheap. 
> -rivish... weird to say, but if anyone, you'll know what i mean. uniquely 
> pretty, versatile, not overly mechanically complex, able to carry a small 
> load and do more than one thing well
>
> So far i've been looking at late 70's/early 80's off road yamahas and 
> hondas. 
>
> Anyone have any online resources, makes/models/years that would work, 
> thoughts, ideas etc. 
>
>

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