As per usual, this site is offering you some great advice. Jeff H pretty well nailed it.
I'm thinking about learning curves. Competence under sail comes with determination and experience. It's a fun learning curve, but not to be underestimated. Being able to handle a cruiser safely under a variety of conditions is learning curve 1 that you'll have to deal with. No shortcuts.
Learning curve 2:
Boat ownership and upkeep is another learning curve altogether. Maintaining current systems takes time to master (I'll let you know when I master it). Evaluating where upgrades and mods are required, and effectively implementing is another. Knowing what needs attention is part of this learning curve. My first cruiser was a 1972 26 footer. I made a few mistakes with that boat. Not catastrophic, and all fixable, but stuff I just laugh at now. And that's despite carefully considering each upgrade or fix I attempted.
There's no getting away from learning curve 1. But learning curve 2 can at least be minimized to some extent. The teak decks are one example already given. I look at a teak deck, and all I see is hundreds of holes in the deck waiting to leak someday. Brightwork is a thing to behold...on someone else's boat! But that's just me. I'm a woodworker, but I get no thrill from applying 7 coats of varnish. Even without brightwork on my boat, there's plenty of waxing to do, valves to adjust, fuel filters to change, oil to change, cables to lube, shafts to align, anchor windlasses to lube, rigging to maintain...whew. I'm a coastal sailor, so I can't point you to the bluewater boat that minimizes maintenance, but it's doable.
Those who have suggested that your first boat will not be your last (or even be your boat in two years) are so right. It's just unavoidable. Inconvenient, but unavoidable. Not that one couldn't strive to get right the first time. If you do... write a book.