i like the fat bob more, its closer to the highball msrp too. where the street bob is right close to the vegas 8ball price.
If you really want the HighBall look, its cheapest to just buy the HB, if you hadn't stated that you plan to leave it relatively stock, i would agree with Half crazy and say to get a vegas 8-ball and do your own customizing, might cost alittle more in the long run but it would be custom. (your not going to put paint, wheels and bars on for under $2k unless you do all the work yourself and find a hell of a deal on the wheels and thats still pretty tough)
i'd guess and say cost of ownership would probably be the same over over a 2 year span. ride'em both and see what you like.
2007 Hammer S 100CI
S&S air cleaner, PCIII, SRVT clubs exhaust, Avon grips.
2006 Kingpin 100CI
stage 1, touring setup to come soon...nm bought a XC.
2013 Sunset red and black XC