Have a thin water situation here in FL similar to that of the OP, though without a trust fund for a "starter" boat that is apparently envisioned by mr_f.
As the OP is a flying scot sailor I'm guessing that he'd prefer a faster boat that sails well in lighter air, vs. a cruiser type. If so then S2s (6.9, 7.3, 7.9) are good boats to consider. Catboats are stable and salty, but are usually heavier w/ no headsail and so not as fast. Others to think about are Balboa 26, Precision 23, and Tanzer 7.5 or 27 SD. Some of the 23 to 26 foot O'Days have CBs and are a consideration as well. These boats can all be had for $5-15K, depending on features and condition.
That being said, I'm still in research mode, and certainly am open to other suggestions.
Ultimately it depends on what is comfortable for you and the family, and the quality of PO upkeep. Best of luck to the OP.