So many ways to approach getting into sailing and owning a boat. Great suggestions and input so far so no need to add there, but...
I'll share our experience and maybe it will help you? maybe not?
I'll skip the pre-sailboat owner experiences and try to get to the point...
About 7 yrs ago we started looking for a boat, on-line and visiting boatyards. We looked at many, many boats, seriously at a Catalina 27 followed by a Catalina 30. Man I wanted that boat badly, lots of heated discussions about why we should/shouldn't buy the boat. But something wasn't right, so we backed off from the search for a while.
A couple of months later I got a call from my uncle, there was a cheap, P.O.S. 20' Buccaneer for sale for all of $300.00. We bought the POS and were so excited we spent the entire winter, sometimes in the snow, working to get it ready for the coming season. Mostly re-doing teak, polishing, and fixing or replacing safety related stuff like running lights, bilge pump, etc. The marina owner was so happy to have a somewhat respectable boat sitting in the slip vs. the neglected POS that was there
We sailed it for two years before we started looking again, we found our next boat quickly, a 37'er.
Is there a point to the story, I think so...
We waited, got the boat we really wanted, and most importantly (IMO) skipped the saga of buying a 20' boat, followed by a 27' boat, followed by a 30' boat, and so on.
My $.02 FWIW
BTW: We sold the 20' Piece Of S*^t Buccaneer for $1000.00