Sailing a wide range of boats before owning something large never seems like a bad idea. We joined a club in the Portland area that allows us to sail 20-37 footers, and for more variety we can charter a wide range of boats in Puget Sound.
It seems like we all start with the idea that a heavy “safe” cruiser is the way to go, but sailing some of the new designs can be real eye opening. Just last weekend we were doing over 7 knots in moderate wind in a modern 37 and having a great time.
So, owning in the long run is great, but sailing everything you can beforehand is a fun experience — and don’t forget to give the lighter, fin keel boats a chance.