live on/learn on/cruise on
You are thinking very clearly! If you will be comfortable in a small boat, go for it! As Ken said, you will get a lot more use out of it...and the costs will be far less than larger vessels.
I like Cals a lot...that would be a workable choice for you. Check out the Contessa 27, which is a tried and true boat. The Flicka is also a nice boat--it''s 20 feet, and I''ve known several couples who have cruised aboard one. There are many more good choices....if you will be in the Seattle area, I''m sure there is an excellent used boat market there that will fit your needs.
One resource you might want to browse is www.pocketcruisers.com, which is devoted to boats in your size range.
S/V Nehalennia (Baba 30)