Hi Mark!
So I've bought my first boat this year (a Pearson 26), and gotten deep into local racing (not with the Pearson). My recommendation is, if you're gonna teach yourself to sail, don't do what I did. Instead, buy something small (< 19 ft), used, and trailerable. Here's why:
Books will teach you a fair amount of what you need to know, but experience is essential. The maintenance book you want is Don Casey's Complete Illustrated Sailboat Maintenance Manual.
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Do that for a year, get really good at it, and then start shopping around for your first cruiser! Catalinas are absurdly popular, and parts are plentiful.
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Sailing is an ABSOLUTE BLAST. Welcome!
Don Casey has two useful books, still in print and readily available, I believe: Inspecting the Gimg Sailboat, and Complete Illustrated Sailboat Maintenance (which may actually include the first title). I believe they are aimed more at larger boat systems (including electrical, engine maintenance, etc.), but the sections on rigging, deck repairs/recoring, etc., should be useful to anyone.
Don Casey's Complete Illustrated Sailboat Maintenance Manual: Including Inspecting the Aging Sailboat, Sailboat Hull and Deck Repair, Sailboat Refinishing, Sailbo https://www.amazon.com/dp/0071462848/ref=cm_sw_r_apan_glt_i_J8K6W7ER51EVNWNGAB59
You may want to pickup Don Casey’s book Complete Sailboat Maintenance Manual. It’s a great resource and has an entire section on inspecting an aging sailboat.
https://www.amazon.com/Caseys-Complete-Illustrated-Sailboat-Maintenance/dp/0071462848/ref=nodl_
I used to have a Catalina 22 and a 30. Both were easy to handle and fun to sail. I’m sure the 27 will be the same.
Good Luck!
That combined with whatever documentation exists specifically for your boat means you probably won't fuck up anything bad enough to require multiple replacements in a short timespan.
I'd be surprised if you haven't already been recommended this book a million times, but it's pretty much answered every question I've had as I've worked on my boat (including everything related to varnishing): Don Casey's Complete Illustrated Sailboat Maintenance Manual
This is the Bible:
Don Casey's Complete Illustrated Sailboat Maintenance Manual: Including Inspecting the Aging Sailboat, Sailboat Hull and Deck Repair, Sailboat Refinishing, Sailbo https://www.amazon.com/dp/0071462848/ref=cm_sw_r_cp_api_i_pXGeFbZZTF2S2
Also good:
Marine Diesel Engines: Maintenance, Troubleshooting, and Repair https://www.amazon.com/dp/0071475354/ref=cm_sw_r_cp_api_i_bYGeFbNVKM8AV
I recommend this book if you want to understand what the scope of maintenance on a boat is:
Don Casey's Complete Illustrated... https://www.amazon.com/dp/0071462848?ref=ppx_pop_mob_ap_share
If you want to buy your own boat then really get up to speed on the kind of maintenance it will require, and be ready to learn the systems onboard.
Buy this book
https://www.amazon.com/Caseys-Complete-Illustrated-Sailboat-Maintenance/dp/0071462848
and this book
https://www.amazon.com/Boatowners-Mechanical-Electrical-Manual-4/dp/0071790330/
Too many doofuses have lost a boat because they don't know how to close a through hull valve. Don't be that guy!
Nothing wrong with soap and water with a little bleach, and a scrub brush. I like Simple Green citrus cleaner concentrate, lemon scent, in a big jug. Aggressively scrub and rinse the interior and exterior. Before you get a lot of water in the boat, make sure the bilge pump is replaced or at least works, and wired to a battery so that the slop that goes into the bilge will go outside easily.
Throw away all cushions and textiles on board. Learn how to sew and get a used sewing machine - this skill will really set you free on a sailboat.
Throw away any rotten wood, being careful to trace patterns for replacement. Cut new panels out of appropriate plywood, learn to varnish and do simple cabinetry.
Discard all running rigging, one piece at a time, replacing it with new rigging of the same diameter. I've found the best place for running rigging to be ebay - make sure you buy low stretch line suitable for halyards. Sew new to old, end to end, and pull the old piece out and rerig with the new at the same time. Have a rigger replace the standing rig while the mast is down, or go whole hog and (with help and advice) learn to rig your own boat. Rewire the mast for required lights and an antenna if you want one up there. Replace or at least remove and service any through hulls. I don't know if you have a marine head or not, but this will need service, and the piping will need replacement.
Batteries - check out the many excellent youtube videos done by Jeff Cote at Pacific Yacht Systems. It's almost an online career training course on boat electronics. For your purposes, 2 quality deep cycle marine flooded lead acid batteries will be fine. You'll get good life span and utility at a good price. You can get them at WalMart or Costco or any auto parts place. Wear these out before you automatically assume you need something "better".
Boat hulls use 2 kinds of paint - "topside" paint, which is the colored portion above the water, and "bottom paint" which inhibits weed growth and goes below the waterline. Research paints used in your area and get a gallon or so of decent quality bottom paint and watch youtube for "roll and tip" instructions. Check out Jamestown Distributors and Ultimate Boat for reasonably priced paint. Sticker shock on boat paint is part of the fun you're in for. If you can't work on the boat where it is, you'll have to find a marina or other location that will let you work under the boat - many will not allow this. A full paint job (topside and bottom) for a 26' boat will not be cheap but done well it can last many years. Bottom paint alone will have to be done probably every 2 years and is less expensive. Decks can be pressure washed and scrubbed, then repainted.
Make sure the rudder is solid - pay particular attention to the bearings and that there are no cracks allowing water in (other than small cracks in the paint.)
Sails will be useless - discard and look into either buying good used ones (look for used sails online) or have a sailmaker make you a set. For a popular boat like yours I'll bet that you can find decent used sails that will get you started.
Hope this helps, don't try to eat the elephant all at one time, and don't spend a dime more than you have to on fancy crap you see blue water cruisers using - just make your boat into a safe and fun boat for local work, use it and have fun with it, then branch out slowly from there. Fancy unnecessary electrical stuff is where the money really stacks up. Have friends help you - buy a couple cases of beer and let your boat friends show you how much they know. In a few years it'll be your turn to help someone else.
Wow, missed your comment sorry,
For $200 a month you would need a boat mate, I have 3 friends who share a 27 foot catalina so it's possible.
Not much is needed to buy a boat, just some savings or a student loan ;)
Once you have said boat meet people in the marina and talk to them about learning to sail, most sailors will be happy to have another person who is passionate about sailing on board.
You need to learn to cook and live in a small space, and share things like a bathroom shower and a dock.
Check craigslist and call marinas about boats in the rears (past due on rent and given up) find the boat you can afford, not what your dream boat.
Get the boat and buy Illustrated guide to sailboat repair
You should get a sailboat because most sailboats over 27' are designed to be taken on cruises and/or lived aboard. Most power boats are not, they are designed for day trips and such.
Any other questions and or comments let me know, if you wanna check out my digs pm me or join the SD facebook redditor group