If you're going to
race it consider not only the initial cost but the cost of upgrading an older boat (traveller/jib cars/solid vang/standing and running
rigging and, most of all...sails). Monohulls that come to mind that have a good turn of speed are
Santa Cruz 27, J27, J29 or, a little older, Evelyn 26, Lindenberg 27 and in my opinion, the best...S2 7.9(26'). These are almost all
outboard powered and there's plenty of used stuff (boats and hardware) around. Look for soft decks on all of them 'cause
hardware is always shuffled around on older race boats and, if not done right,
water seeps into the
deck core. Use the plastic hammer test (sharp
noise for solid laminate and kind of a dull thud for waterlogged). Especially check around stanchions and anyplace
hardware has been moved. Probably want to consider a
survey or get a copy of Casey's book on
Buying an Older Boat. To source one, I'd check eBay also as there are occasionally great deals on older racers. Have fun.