Height and weight of you and your passenger may help...
For $6K, you're looking at something used, so the final choice may end up to be what's up for sale at the moment.
Here's a decent '99 Dyna Wide Glide for sale at $6,000. http://www.kijiji.ca/v-street-cruisers-choppers/muskoka/for-sale-harley-davidson/1103499835
I'm 5'9, combined weight of 320lbs.
Been riding on the street for 6 years. Only thing I've owned is a 2003 r6.
Definitely looking at something used. Been looking at the prices for vstroms and they are right around my budget, but it's not set in stone, will check all my options before I make a decision.