I am about to acquire a ICW lot in NC with fairly shallow water that my older Hunter 27 just doesn't fit. Bid on and lost a Gem 31 and have been eyeing an older Iroquois 30 that we can use for a floating weekend getaway but still enjoy sailing. I don't think the Stilletto 27 will keep my wife happy. What other older but fun to sail cats do I want to be looking for with a $20K budget?

$20K is quite small for something that size. BUT, I've seen a few "Crowther" (I think thats how you spell it) tri-marans in that range. One recently on ebay. Be sure to check the soundness because it would probably be a woodie. If its built right then you should have no problems. I have a Stiletto and can attest to the attributes of those. A cruiser its not other than short stints. For outright comfort you'll need something larger.

JMO,

Clayton

The Gem 31 sold for $18,000 (I was out of the country otherwise I would have got this one), A 1975 Iroquois 30 just sold for $19,000 (photos looked good, buyer is quite happy with it) and south FL has a Oceanic 34 listed for $25K. So while $20K is small, it is not unreasonable. I al open and looking for leads / suggestions.

You will be very lucky to find anything good for that money.
Some folks have bought MacGregor 36 cats (normally around $20,000) and added a cabin pod. Pretty darned fast boat, but probably not after adding a lot of weight.
Rick