you can get a decent 25-30' old junker for like 4k. Try and find someone to check out the rigging. A slip is going to be pricey. Like 2-4k per year depending on where you are. Insurance is cheap for sailboats and usually marinas make you keep a pretty big policy. First boat owners i think they charge you more but should be like 300... Im guessing here. I pay like 250 for my old 30 footer. Try and look for something powered by an outboard as worst case scenario you might have to replace that which can be anywhere from like 1-4k for a decent used one. Bottom paint is like 900-1.5 k but have em put an extra gallon around the water line and you should be good for every other year if not every three years if you dont mind having an ugly bottom for that last year. Most older sailboats have water damage of some sort. You mainly want to make sure the main structural interior bulkheads arent completely trashed. A little soft wood around the chainplates is most likely not a big deal but significant damage can be a red flag. The chain plates are where the mast supports are attached to the hull. If they are actively leaking, rebedding with some butyl tape is pretty easy and last a long time. It used to be regular maintenance to remove and reapply sealant at these points but the butyl tape makes that way less of a headache. Try and look for a boat with a furling jib but make sure the furling device actually works. IF the seller doesnt want to take you out at least make him unfurl the jib and raise the main just to get an idea of the sail and rigging conditions. Replacing sails can be a pain but will likely be needed at some point but you can usually find decent used sails for like 300-600. If you are willing to learn and work on the various systems of the boat yourself you can save a ton of money but if you plan on having other people do all the work, pretty much everything gets real expensive, real quick. Apparently hull/keel damage is a significant concern as well but I think since I live in the soft bottom Chesapeake, I have never had any issue. I went overboard and gouged out any cracks and drilled drainage holes in my keel when i got my old junker but luckily it was dry. And just slapped on a bunch of filled epoxy per the west systems manual. But I probably didnt even need to worry about it. But yeah slip fees are the big expense if you work on the boat yourself and maybe a new outboard along the way. But if you keep the boat in sailing shape you shouldnt have trouble unloading it after a couple years. If you buy a boat from the mid 80s or earlier, you will likely have a bunch of nasty looking exterior wordwork with bits of old varnish. This can be expensive to have redone so i just used a heat gun and a scraper and removed it all and use semco oil to keep it nice looking. The topside paint will likely be chalky and having the topside painted can be super pricey, but soap and wax will keep you from being too embarrassed at the marina. Also look for soft spots on the deck. if there are a couple small ones near ports or deck hardware you should try and first fix the leaks then fix the softspots. replacing the deck is another crazy expensive job but once the leak is fixed and ins not a huge area, you can just drill holed and fill with epoxy. I wouldnt try using a boat like this in any serious weather if you havent have the rigging properly inspected but for a day sailer to play around with for a couple of years you can definitely do it without breaking the bank. I also dont recommend a partner unless they are super handy and super excited about doing lots of work on the boat. This can lead to huge headaches outside of the financials of it all. If you are in MD I know of an old 30' newport that will be listed early July. No clue for how much, but a buddy just inherited a 35' bristol and he needs to unload his current old junker. That being said, once you get around the 7-12k range, the options get WAAAAY nicer