When I researched and bought my first keelboat, I met a lot of blokes who'd bought a boat expecting their partners or family to come sailing but who found in the end they didn't want to. Not to be deterred, I thought to myself - I'll buy the biggest boat I'd feel comfortable sailing solo, and fixed on a 30' Ted Brewer designed cruising boat. Now that I can handle that fairly easily, I might consider a 34' or thereabouts, but probably not much larger. For example, I was looking over an Adams Traditional 36 at the time and the owner said "sometimes it takes all of my strength to winch in the genoa sheet". You can have power winches etc, but that's just another thing to go wrong. So you might want to consider something smallish, and then spend the money to make sure all of the various systems are working - electricial, rigging, engine and so on. I bought a boat with an almost new Yanmar in it for practically the prices of a new engine install, so the boat was thrown in for free - that's important as many cruisers say they end up motoring one third of the time. My fairly limited cruising history bears that out, both in my trailer sailer and now in my keelboat. A lot of yachties enjoy working on and fixing their boats, so if you have that inclination you could do worse that to buy a solid old hull and go through the steps of upgrading the engine, electrics, rigging etc. Expensive, but then when you're at sea and something goes wrong you'll know what to do. One boat that I really liked was the Arends 33, which would fit most of the criteria above - right age to be cheap enough, shallowish draft for entering bays etc, enough room for a couple to live comfortably and just at the outer limit of what I'd regard as a comfortable boat for berthing and handling when the wind is up. This old ad gives the general idea ...
www.dbyboatsales.com.au/listing/arends-33-6/ If you're going to have a high-earning career, you'll be able to get any boat you like but for many sailors I know that's not the point - getting something modest and making it your own is a journey in itself, before you even head out to sea. And one more thing ... as the renegade designer George Buehler pointed out in his books, obsessing over this point or that point might suit racers, but for cruisers "sailing's supposed to be fun!" So enjoy...