Bill - Great Info - thanks for the content. I ended up getting a 2014 Vstar 650 Custom (see http://www.motorcycleforum.com/189-cruiser-forum/190386-what-your-first-bike-would-you-recommend-new-rider-2.html#post2373193).To the OP, I would opt for a bike that was a standard at first, something a bit banged up but serviceable (so that you won't be as downtrodden when you scratch it), and something that you can work on, so something a little older rather than newer. I also would say keep below that liter displacement to keep insurance (and your insanity tendencies) at bay.
Another thing, make sure the seller has clean title in hand of course, and be sure that if the bike has to have work done, you are willing to do it yourself, or at least can get it done cheaply. Dealerships can be insane for cheap bike repairs. Also, how well the mechanicals and electrics work are FAR more important on the first bike than cosmetics, in my opinion. With the right bike, you may be able to resell it for what you bought it for, and come out even. That won't always be the case, of course, but on older bikes, that seems to be the advice I keep seeing and what I have witnessed personally with people I know (though I have not yet sold my first bike yet, so I do not know first hand this specific experience yet).
If nobody has told you yet, be DANGED careful about Craigs List bike offers, and make sure that you have the seller at the tag office, with the bike AND the title before you offer up cash. Nothing like a bad transaction to sour you on your new bike (that has the wrong title, or a faulty title, etc.) and your cash is gone. Or worse, the seller took your cash AND the bike and now you are hunting the butthead.
I have seen many reports that you don't generally get much if any extra for things you bolt onto a bike that you later sell, especially a first bike type unit (due to the dings already on it plus the ones you will likely add), so be frugal on the farkles to the things you really want on there for you to use, not for some future person who will likely have farkles of their own they want to obtain. Saddlebags are nice, but not every Ninja owner wants them. The bank often could care less what aftermarket goodies are on a used bike if the dealer did not install them as a factory option, so save your ducketts for your next bike rather than going insane on your first one, if you are at all likely to trade up in the near future. No point donating all that chrome to the next rider unless you are just that nice a guy/gal.
I liked the balance and height of my standard, but some like the nimble crotch rockets or have shorter legs and cannot ride a UJM easily. I cannot easily sit a Ninja because of my long legs, and they don't match my style. That Buell Blast (they were 500's or maybe 550's??) they used at the MSF course was darned hard for me because it had too short a leg room capacity. However, a small displacement bike can be fun if you don't weigh as much as I do and have the flexibility to be able to ride it comfortably.
Beware of bikes that put lots of weight on your arms or cram your legs under you as you ride. I prefer to let the bike support me, not forcing my arms or legs to support me. About the main snag I have with my Honda is that I have to sit a little like a bird on a roost when riding it, and that it gets crampy on anything more than about a half hour or so at a time. The pegs are just too high for me. I installed freeway pegs to counter that, but I have not yet gotten that danged bee up the leathers either. Another bonus that Dave left me his Intruder VS 1400 - at least I can relax a little now on longer trips.
I also like a windscreen, but be cautious about how that screen is supported, because those that have the two prongs supporting them (the sports screens with two aluminum rods holding them up) can be damned dangerous if the screen breaks, especially if you are not riding with a VERY thick leather jacket... Ask me how I know...