Sportster 883 or Kawasaki Concours?

I'm actually not sure you could pick two bikes that are more different. I have a decent amount of experiencing riding BOTH of these bikes. By virtue of your size, and the sheer flexibility of what it has to offer, I would suggest looking more seriously at the Concours. That being said, and you didn't mention what year it is, I would think you could find one for a little bit cheaper than $5,000. It's regarded as an "old" (and it is...25 years with essentially no changes) design, and it is not terribly sought after, especially because of the antiquated appearance. Most sporting riders demand the latest, most cutting edge components available, but if "pretty decent" is good enough for you (and considering that you're contemplating the purchase of the 60-year-old-technology-laden Sportster, I surmise it is), the Concours is a solid steed. Plenty of power, very smooth in-line 4-cyl. that is a tried-and-true design. Very neutral, upright riding position with decent ergos make it a comfy day-long mini-tourer. You can pull the bags off for a sporty look or leave them on and you have something practical. You can even get a Givi box or something similar for the back if your penger wants a backrest and some more storage. All that being said, the much-maligned (by non-riding neophytes) 883 is a great bike too, but is much better suited to shorter around-town jaunts, and has limited promise for any types serious two-up riding, and day-long excursions. A nice little hopscotch-er, if not a wee bit small for you, physically. You can't really go wrong either way. BOTH will be fun, but the Concours will do everything the Sportster will PLUS a bunch more, and probably wear you down less while putting a bigger smile on your face. Good luck!