As someone who grew up cruising on a sailboat. And I'm sitting at anchor now in Panama... Sailboats if done right are not expensive. Less than rent for sure. I figure 4k a year in maintenance, on average it is less than that.
A few tips I will share.
1. You need to want to, and enjoy fixing things. You need to be able to diagnose problems with the engines and pumps etc. Then get the parts and fix them.
2. Your size range is great. Bigger is not better. We have a 35ft center cockpit w/aft cabin. Was perfect for our family of 4. For week long stints it was OK for up to 8 people. As an owner of a 40 yr old boat, you really want to focus on hull integrity. Any delaminating would be a bad sign. (Please buy a fiberglass boat, 100%) There are lots of option in your price range. Mostly monohulls which are the frugal choice anyway. Only one motor, etc.
3. DON'T get a boat with teak decks. NO TEAK DECKS.
4. On a fiberglass hull. Brightwork does not have to be nice. It is superficial, for looks only. BUT, if you want a perfect gleaming paint job... It can be a lot of work. A REALLY lot of work. In the sun, with chemicals that may cause cancer in California.
5. If your desire is to not spend time at the dock. Doing things (fishing/diving/snorkeling etc) get a good dingy. This will make ALL the difference. I would recommend a 12' RIB. If you don't have davits to store it, you will need a more compact storage system. We have seen some many failures (some our own) in this matter.. Our second inflatable is the Achilles SG-124. Still going after 20 years of 6 months a year in the sun and hard use. Pair that with a 15hp, covers water at 22kts. We resupplied for 2 years 40 miles from the closest town. Every week 80 miles round trip. This is the biggest gear related recommendation, I can't stress it enough. You want a dingy that you can stand on the edge and lift water/fuel/groceries without it flexing all over the place. The Achilles has an aluminum locking floor, it doesn't flex. You can't get a wood or inflatable floor to be stable enough to work from. They squish when you walk, don't plane correctly with weight in the boat. I can go on...
6. Keep systems simple. Do you really need that expensive chart plotter? Electronics will fail, get stolen, become outdated...
7. When outfitting the boat. Get ample solar power, maybe a wind generator. They will pay for themselves, you don't want to run the generator/main motor w/alternator 2 hrs a day to keep the batteries up for the refrigerator. Start with 250 watts... maybe add more. You will need to figure out where to mount them, that is the challenge.
8. Go live your dream. Come see me in Panama sometime :)
There is a well built Ingrid? <-- pretty sure on this.. 38 in the bay here. The guy has about 10k in it. He would sell for that, most likely less. It isn't pretty, but a very well built and easy to maintain cruising boat. Boats can be substantially cheaper depending on where they are. If you want a real bargain, look in the South Pacific, or here in Panama... Equador... anywhere that people end up, and are finished. That is the time to be standing there, buying. The east coast of the US can be good as well, there are a LOT of boats to choose from.