A nice sounding plan! We know a few people who did multi-year cruising and some doing half year cruising. I called it, "retirement on the installment plan".
You might consider looking for a Nor'Sea 27.We lived aboard ours (Jill and I) from 1996 to 2008 full time. We cruised from 04 to late 08 down the west coast. They are not as low a cost as many, but more capable.
BUT, the beauty of the boat is that it is capable of circumnavigating (many have) yet can be stored on a trailer to be towed (by the owner) cross country when wanting to go to weather at 55 MPH. Also when not cruising, it's VERY low cost to store close to home, even when far from water.
Just an idea!