Keep an eye out in classifieds, cycle trader, craigslist, ebay and on all the dealer websites (within the distance you want to ride). Also there are at least 3 other Victory websites other than this one that have classifieds. Look long enough and hard enough and a deal will fall into your lap.
Are you current or prior Military? If so Victory has $1000 waiting for you. Have you looked at the Demo Truck schedule? If not, do it! I'm not sure what the deal is this year but last year they gave coupons for $1000 off a new Victory if bought at that dealer within 30 days.
If you have to buy used don't sweat it; Victory is nothing like Kia or Hyundai -- these bikes are tough! I read on another website that only a handful of the Victory's produced have had internal engine problems; Victory averages building 33000 bikes per year -- after over 10+ years it's tough to find a bike that had the engine opened for anything other than a big bore kit!
I'm biased towards Cross Roads, I payed $14,999 (and got $1500 in accessories thrown in) and love the bike so much I would do it again in a minute. Best part is that I wasn't in the market. My wife started riding around with me on my V-Star and decided "we" needed a bigger bike -- it was a Christmas miracle (in August)!
Best of luck, hope to see you bragging about your new ride soon!
Retired USAF, IYAAYAS!
2008 V-Star 1100 Custom Bobber project
2011 Crimson XR with Forged Highway Bars / Hard Bags / Passenger Backrest, Ness parts including Smooth Layback Plate Frame/Mount / Rad 3 Mirror / deep cut grips / drivers floorboards /shifter peg / brake peg / passenger pegs. Witchdoctor black rack, Lloydz filter / timing wheel / VFC III, 7Jurock windshield, Drag Specialties seat.