The old salts don't like when the nubees don't agree. So I'm going to keep this light on advice. in addition my situation is somewhat different but somewhat similar as well.
I am 62 and decided to try sailing, something I wanted to do for a while. serious budget
limits. so... I looked for months til I found what worked for me.
1. I had to make compromises.
2. I found a good solid boat that I know needs things.
3 I made a list of things that cost big. roller furling
etc. I then prioritize and plan to add those things over the coming years.
4 I couldn't afford what I wanted straight up but I own a solid boat and can upgrade.
5 like yourself I didn't want to buy several times, rather get something I can enjoy while I accumulate funds for the next most important thing.
6 common wisdom says that you will never get your investments back. true but beside the point. the point is to enjoy the experience.
I bought a 1973 morgan
OI 33. old but well maintained by a man who owned it for 37 years. it was his baby and he took care of it. these boats are out there. I paid 10k and will pay another 10k for those big ticket items. but I had 10k to buy. not 20k.
I bought in NJ, took lessons and motored it to NC. sailed it a little but because of conditions I mostly motored. 11 days down the ICW
. fun! HARD (single handed)! an enormous amount of work. a few terrifying experiences. I handled many issues as they came up. It is an old boat that hadn.'t been on a long trip in a long time. but I did it!
You can too. don't let the curmudgeons get you down.