I had rode an older ultra and had a 2010 that i put 25k on in 3 years. go with the newer 12 bike. the ride is going to be quite different since they redesigned almost everything chassis and exhaust wise in 09. cooler riding for passenger to. better heat management and better feal and handling due to the chassis and bigger tires.
I recently went with the 2012 Road King....what made me choose that as opposed to other, older models I was considering...1) warranty, 2) by the time I finish paying off the finance, it'll still be a "new-ish" bike. 3) things like ABS brakes, cruise control etc that comes with the newer bike.
I have 2 friends who bought 07 CVO Ultras. Big probs with head gaskets. Also compensater bearings had to be replaced. Also has the square cut 5th gear which has a very loud whine. HD says its normal. Don't know if the 08 CVO 110 is "factory repaired" versus the 07 110. I'd check that out for sure.