Oddly enough, my wife is more prone to 2 ft-itis than I am. Don't give her any ideas!
A fascinating thread. We joined our sailing co-op 15 years ago, starting on O'Day 20's. We took our son with us and had some interesting "teachable moments". As time went by, we upgraded to the club's Catalina 27's and our son developed his own interests as he grew up.
Two years ago, we finally took the plunge and bought our own boat, upgrading to a Mirage 29' sailboat. While bigger boats were available, a key factor was selecting something that the two of us could manage, and eventually do most of the work on as we gained more experience and confidence.
We are still in the process of learning, and adjusting the boat to fit our needs. Last year's big project was the furling system and dinghy purchase. This year's big project is the rest of the rigging. Next year's list is already being compiled.
I knew these types of projects were likely when we bought the boat, and I'm happy with it. This also makes it much easier to resist The Admiral's 2 ft-itis. I'm in my happy space!
To the OP, I would suggest that you are in your own happy space with the boat that you presently own. That said, if you are prepared to spend the time needed to make a bigger boat your own, go for it! Some folks are quite happy doing that. However, if you aren't certain (your original post suggests some uncertainty), why make a change.
Whatever you choose, all the best.