As far as price, Plan to spend "more" for one is my advice, you get what you pay for. In a recent boat search I was trying to limit the top dollar, and then realized that much better and newer boats showed up when I went up about 20% over that. So that was my budget versus taste battle over price points. What you have relayed thus far shows you can relate to this, even though 15k vs. 40k is a little more than 20%. But you can definitely see the difference between those boats being compared one on one, right?
Regarding jumping right into a cruiser, I never really wanted to boat that way so won't respond as directly to that, others here have given very good insight along those lines. My brothers always had/have RV trailers, one is fulltime travelling camper now. There is a learning period with camping like that, and they both got pretty savvy with it. It is the same with Marine Cruiser "camping", even more to learn. Both of them started small, and traded up as they could. One changed it all up and went with a Cabin property on a small lake, the other is fulltime retired traveller, sold the house and all. So it is a process, not sure how many steps can be skipped.
I was always drawn to the "look" of a pocket cruiser, but I know that my boating usage is just day running about and water sports. One of the last boats I had was a 22' Cuddy and we just treated it like a bowrider mostly, except you couldn't just drop off or pick up nosed in
Never overnited, it was chosen as it was a pretty Okay deal on a Repo for slip fees. Nice idea for the Cuddy, and had a blast in it, but looked at bowriders the whole time I had it. But that's me.
Now as to looking ahead to my "final" boat, I (now at 64 years) decided recently to go newer and replace the 2 older boats I had. I know what 90% of my boating has been, and it was pretty constant through the years, so a 19-20 foot bowrider was the ticket, O/B or I/O, either was ok. Ideal boat would be on a single axle trailer. I had neglected myself for years, and had the gamut of old obese guy problems with HIGH blood pressure, type 2 diabetes, cholesterol, all that. 3 years ago I went to the Doc and started to get after all that that because I was tired of going to the bathroom every 1.5 to 2 hours. Got the diabetes under control, blood pressure was stubborn but getting better, and lost a lot of pounds due to diet changes. Then about 8 months into that I had the stroke. Whole right side went dead for a few minutes. Had lots of smaller ones too, those affected my eyesight and talking, that was humbling. My dyslexia became greatly magnified, my signature changed, wrote down the wrong letters when writing anything, struggled with simple procedures that before were afterthoughts, all that. The mobility came back almost immediately, but the cognitive stuff took about a year. Anyway, started feeling much better than I had in years and decided to do a boat replacement. Almost like physical and mental therapy to stay sharp, and see if I still "had it" (previous lives in Hotrodding). Kids in college, wife in college, etc. so had to finance most of it even after selling the other two. But that was my choice to get it done before I can't. Wife agreed, just wanted a nice non-stinky interior this time
Most importantly, Keep yourself up healthwise if you don't now.
Boating-wise, with good choices you may be able to find that one final boat now, but probably not. With a good purchase deal made on a newer more expensive (and more desirable in the resale market) one though, you could get out of it with a small-to-medium hit if you need to, and post it under the learned lessons column in your ledger. Or go with a "trial" boat (also renting at first seems prudent with the cruisers) then trade up once you have decided you (both) are fully into it.
Good luck, nice first world problem to have in my opinion!
