Originally Posted by SloMo228
What about an older CL350 scrambler or similar? They're easy to find for well under that price point, for $1500 you can probably find one in very good condition. Smallish bikes with a low seat height, pretty sure you can find one with e-start, they're definitely street legal and more road-oriented than any dual sport, but he'd still be able to ride it on gravel roads. Plus, they're pretty cool-looking.
I think I know what bike you are speaking about but aren't they kick start only and fairly old? He's not a mechanic and getting a CL350 in decent trouble free condition are not easy to find around here plus wouldn't he be on ebay for parts?