I’ve been dreaming about owning a sailboat for years, and I think I’m finally ready to take the plunge. I’m a first-time buyer, so I’d love some honest advice from people who’ve been through this before. My plan is to use the boat mostly for weekend trips and short coastal cruises, with the goal of maybe doing something longer (like the Bahamas or down the coast) in a year or two once I build confidence.

Right now, I’m looking at boats in the 32- to 36-foot range — older models from the late 80s to early 2000s. I’ve seen a few Catalinas and Hunters that look decent within my budget ($40–60k), but it’s hard to know what to prioritize. Some listings look beautiful inside but mention “soft decks” or “original rigging,” while others are uglier but claim “recent survey, new standing rigging, and upgraded electronics.”

What should I really be looking for as a first-time buyer? I’ve read that a solid hull and dry deck matter more than fancy upgrades, but how do you tell when a “minor moisture issue” becomes a big problem? Also, how realistic is it to handle basic maintenance myself if I’m fairly handy but new to marine systems?

Any particular makes or models you’d recommend for beginners who still want something capable of offshore cruising someday? I’d rather not buy something too small and outgrow it in a year.

My first advice would be to read some books like "Get Real, Get Gone" and "Twenty Small Sailboats to Take You Around The World." These books helped me choose my boats. They argue for safe, seaworthy, traditional designs. It's a good idea to steer clear of boats designed to sell instead of sail. The bigger the company, the more interested in profit they are (in general). When I was looking at boats for the first time, I was looking at small Cape Dorys (27, 28, 30), and similar boats, and ended up with a Dufour Arpege, a 30' boat with fin keel and skeg-hung rudder. I was very happy with that boat. I recommend to look at all the listings that catch your eye, then look up the boat and see what kind of reputation it has. Without a good reputation, you won't be able to resell it. I resold my Arpege quickly when it was time to get a bigger boat. If you are interested in bluewater cruising, I would recommend a boat designed for it, and not a boat designed to win races. There's a big tradeoff. Full keel boats are safe, comfortable, forgiving, and track well. However, they don't steer well in reverse (only an issue in marinas) and they take a little more wind to get moving. Fin keel boats are more nimble, point higher, are lighter, and they steer well in reverse, but they are less forgiving. Fin with skeg rudder is a good tradeoff between the two. But whatever you choose, make sure and read all about the model before you buy.
Regarding your question about deck soft spots, small soft spots aren't a big deal to repair, but big areas are a big deal and should be avoided.
Regarding your handyman experience - go for it. You'll learn.