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Fixed keels on 'trailerable' boats can be problematic with ramp launching. Often the ramp isn't steep enough to float the boat before the tow vehicle is in the water. Extendable trailer tongues may help, but that can complicate things a bit too.

Swing keels or drop keels would be preferable for that reason. For open water (not offshore, but somewhat exposed to weather) you'll want to be sure the boat has a self draining cockpit.

You have a reasonable budget - esp in today's used small market. The venerable Catalina 22/25s would do, plus giving you the ability to weekend/overnight on occasion. For more performance there are some S2 boats (7.9?) that are lift keels too.

Here's a small sample:

trailerable (Sail) Boats For Sale

btw, knowing what areas you intend to sail will affect selection and suitability...
 
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