is buying a used “starter yacht” even worth it for weekend cruising??

so i was at a marina party last weekend, squeezed onto a buddy’s 32 ft express, and realized my little center console is getting way too cramped for how many friends or family i drag along now.

i’ve been lurking listings for a while, mostly 35-45 ft flybridges or convertibles for coastal cruising nd the occasional Bahamas run. Budget is like $300k-ish, used, nothing crazy new. While doom scrolling at 1am I ended up on a few broker sites [HMY Yachts](https://www.hmy.com/) popped up a lot in my searches) and it kinda sent me down this “should I just go bigger now?” spiral.

here’s where I’m stuck: is it smarter to buy a cheaper older boat as a “learner yacht,” accept higher maintenance and maybe sketchy survey results, or hold out for a newer/more dialed-in one with a bigger payment but hopefully fewer surprises? Maybe I’m looking at this the wrong way and the real money pit is fuel and upkeep no matter what.

for those of you who upgraded from smaller boats, what size/age/brand worked out, what would you avoid, and did you regret going too big or too old on your first yacht-size boat??