Some random thoughts and reactions to your posts,
@John6275 ...
With a limit of $5-10k you will have to be patient to find an (older) boat in very good functional condition with a solid trailer and good sails. There are plenty of low priced boats out there that need many 40 hour weeks of repair and thousands of dollars in sails, rigging, resin, paint, tires. Don’t be fooled by an initially low price. Boats like that cost you more in the first few years of ownership.
On a thirty year old boat, you can expect to replace many if not all the blocks on the boat if the previous owner didn’t, including sheaves in the mast.
You may need to rebuild the winches, if the previous owner didn’t service them every season. Parts are hard to find for 30 year old self tailing winches, but not impossible. And replace a traveler car that doesn’t run smoothly anymore. Anywhere that stainless is fastened to aluminum needs to be carefully inspectedand serviced if needed, before it breaks somewhere a few miles from the gulf shore.
It’s easy to look for worn, loose or corroded places on the mast when it’s down. Take advantage of that!
On a light weight trailerable boat, sails that are not old and stretched out are even more critical than for a heavier keel boat. You can still be safe on a heavy keel boat with baggy sails in coastal Gulf waters, , but not on a light weigh trailer sailor. So plan to replace replace baggy sails with new ones! Stretched out sails make even the best boat sail like crappy boat. Sails are the MOST important piece of gear on your boat in terms of staying SAFE when the weather gets challenging.
A new mainsail and 135% furling Genoa for a 25 foot boat such as a Catalina 25 will set you back more than $2000 from a reliable loft. You can buy sails cheaper, but they won’t be built to hold a good shape through 400 - 800 days of sailing.
**** Here is some really important advice: Go spend a couple of days at launch ramps at ***locations you’d like to sail***, and see what people are launching. Talk to a wide range of owners with different boats and ask them what they like and don’t like about a boat. You’ll get a lot of different perspectives. Look inside and at the cockpit layout.
You can have some wonderful adventures boat camping on a small, but coastal worthy Trailersailor. Don’t be obsessed with getting a big cabin. You’ll spend most of you time hanging out in the cockpit.
I have spent many weekends and weeks exploring places all up and down the west coast and inland in a west Wight Potter 19, often in the company of other skippers who owned compacs, precisions, sanderlings, balboas, Montgomerys, Santana 2023s, hunters, etc.
My advice to you would be to buy a boat in really good condition that is popular where you sail,. And you can, if you want, resell in a few years at almost the same price.