We did it
That is what we did. Actually started with a hobie cat for about 1/2 year and would get too wet, so sold the hobie for what we paid for her and bought a Catalina 25 for a little over a year. She was a 1986 25' and got her for $5000, mostly because she needed a bath and a little work, but not much. We did put a new outboard on her ($1400) for a better piece of mind since we spent every weekend we could on her, but you can outgrow a 25 footer really fast spending weekends on it. The trick is not not put a whole pile of money into the small one, just clean her up real good, etc - elbow greese.We then traded the Catalina 25 for a 1987 Hunter 34 and got $8k on a trade-in (the dealer had it sold within a week). We wanted a 30 footer, but the 34s run about the same price. We are upgrading, fixing up, etc. on this larger one since we plan on keeping her for a while now that we know my wife and I both love it. Big boats are much more work and money. I like the idea of testing the waters in a smaller boat and learning maintenance, costs, etc. before taking the leap into a big boat and you will know if you love sailing (and fixing broken things) before wasting much money. With the smaller, older boats, it seems you can typically unload them fast and get your money back - just what I have noticed.