I discovered the main shortcoming of outboard powered sailboats during a recent month with my Catalina 250 in Charleston, SC. When you get into significant waves and wind the propeller get intermittently lifted out of the water due to "hobby horsing", i.e. fore and aft rocking. That cuts the average thrust to the point where 10 hp may not even hold position going into the wind. (In a situation where you are being blown toward a lee shore anchoring may be your best choice.) Water ballast boats are less prone to "hobby horsing" than fixed keel equivalents due to increased angular momentum. But water ballast boats tend to be tender, i.e. more prone to lean in a wind, which may upset your passengers and cause rounding up (unwanted turning into the wind). I wouldn't go larger than a Catalina 22 unless I could park it on its trailer near the boat ramp with the mast up or keep it docked. Look around at boats in use in your sailing area. If you don't see three or four of brand X model Y then it may not be suitable for the relatively windy conditions that are prevalent on the coast. I owned a MacGregor 26-D water ballast and decided it was not suitable for even windy (over 12 mph) lake conditions.
If day sailing is your primary interest then consider a faster moving boat like a Flying Scot, Santana 20 (PHRF 225), and Capri 22 (PHRF 204 to 210). As compared to the slower Catalina 25 (PHRF 222 to 234) or Catalina 22 (PHRF 270). The PHRF number is the seconds per mile deducted from a boat's travel time to make them "equivalent". A J-24 with a PHRF of 168 is an exciting ride for under $7000 including a trailer. It is best stored with the mast up on a trailer.
The Charleston Offshore Racing Association has a 30 foot minimum to participate in their offshore races. I suspect that when there is enough wind for good sailing then the waves are getting too large for under 30 foot sailboats.
If day sailing is your primary interest then consider a faster moving boat like a Flying Scot, Santana 20 (PHRF 225), and Capri 22 (PHRF 204 to 210). As compared to the slower Catalina 25 (PHRF 222 to 234) or Catalina 22 (PHRF 270). The PHRF number is the seconds per mile deducted from a boat's travel time to make them "equivalent". A J-24 with a PHRF of 168 is an exciting ride for under $7000 including a trailer. It is best stored with the mast up on a trailer.
The Charleston Offshore Racing Association has a 30 foot minimum to participate in their offshore races. I suspect that when there is enough wind for good sailing then the waves are getting too large for under 30 foot sailboats.