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Sniff around the bank-owned market, they auction off boats every week. Also keep an eye on yachtworld.com as well as the other popular used boat markets (ebay has some leads too). Deals are out there.
Consider a used world cat. (or similar) super comfort, soild riding and some come with cuttys. For monohulls, I have seen some used gradys on the cheap that might work for you. Older Boston whalers with cutty's might work... The stiger a tad narrow and a little light IMO but the layout is good and they are efficient. Parkers are a bone breaker in seas but have that cutty you are looking for with good fish-ability. I am sure you will find something. IMO there has never been a better time for boat buying...but it is still expensive.
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