Some years ago I commuted regularly on a dual-purpose bike, it was an ideal city bike. Bad pavement, no problem. Parking, no problem. Drop it, so what? And unlike a super-chromulated piece of garage jewelry, nobody steals a Honda XT; they don't even see it. If I were doing that today, I'd look for a Kawasaki KLR 650; that's about the toughest thing around, looks like a motorcycle (mostly), can be had cheap, and is relatively serviceable. Give it a flat-black paint job, and instant Mad Max attitude!
Another great all-'rounder is the previous generation Kawasaki Concours. Based on the Ninja 900 with an overbore and some plastic, they're dirt cheap to buy (you can get a really good one for less than $4000; probably much less), really tough, have the luggage capacity of a pack mule, are a relative snap to service, parts readily available, great user's group at Concours.org (Concours riders are cheapskates and know all the tricks), fast as hell and decent handling, good weather protection, and did I say cheap? Mine had 72,000 miles on it when I sold it. A great bike.
For the vintage look and sort-of experience without the pain, a Kawasaki (why so many from the big K?) W650, if you could find one, would be a stone gas. They feel more like a 60's Triumph than a 60's Triumph. They were extremely unpopular, so when they do surface, they seem to sell for sofa cushion change. Strip off the "Kawasaki" badges and tell everyone it's a restored factory special, with experimental bevel-drive overhead cams.
I think somebody said Sportster; a pre-04 solid-mount Sporty will still cost you a bundle; and contrary to popular belief, won't hold value all that well (those bikes listed in the paper at near new price all have thousands of dollars in accessories. Really. And they aren't selling, which is why they're listed in the paper week after week). A solid mount Sporty is still a pretty good bike, once the necessaries are added (a real seat, free up the breathing), and a lot of people get an 883 for the wife or as a "beginner" bike and end up selling it (relatively) cheap. It'll cost a good bit more, though (whatever you do, don't pay more than $5000, even if the guy throws in his girlfriend), plus which you automatically get membership in the Poseur's Club and will suddenly find yourself craving expensive black leather clothing and skull-motif accessories. In fact, buy my Sporty and I'll throw in expensive black clothing; no skulls, though.