We started looking at that price range and spent last summer in Ontario, Canada looking for suitable boats. It was depressing. Diesel powered boats are too expensive and many of those old Taiwan boats have so many leaking windows they have leaked right down to the area of stringers and fuel tanks, which does not go well. Old rusting steel fuel tanks and even aluminum can suffer significant corrosion after 20 years and they are extremely difficult to replace on many if not most boats without removing major interior cabinetry, or cutting into the side of the boat and modern ethanol fuels for gas engines will literally destroy any fibreglass fuel tanks. New canvas and eisinglass runs 10K and you can imagine the cost of engine rebuilds. Covid boats, those bought for stupid prices during covid, are all coming back on the market, evidenced by latest surveys being in the period 2020-2022 and owners have done no maintenance, nor upgrades and want ridiculous prices. Likely your best bet would be something in the 32-36 range with just one cabin and no aircon or generator, ideally having lived a freshwater life. Gas engines are cheaper, but you have to weigh up how much cruising you are going to do, because they are wicked on fuel. We have a limited area we plan to explore, so are going to gas engines, preferring to suffer the pain of 14 weeks a year of puttering with gas, rather than add 20K to the purchase price of buying diesel. Insurance in Ontario, Canada for old boats is not an issue with a survey. We checked. Hurricane areas like Florida would be almost impossible. Our ex sailboat of 35 years down there was uninsurable in 2020 so we sold it. If you have a mind to learn to sail, there are all kinds of sailboats in your price range that you could have a lot of fun with. They are usually diesel (but sometimes not) and super economical to run. We got 400 miles on a 18 gallon tank, Just watch the length of keel for your cruising area and bear in mind they can be tricky to dock without a bow thruster LOL.
