CHARTER is the slam dunk correct option. This is based on your given condition that the money is about a wash. Even if that includes paying to have somebody do all the maintenance, chartering is the way to go for this reason:
You get to have a nice boat almost anywhere in the world that you would want to sail. Lets' say you want to sail the Windwards, then Tahiti
next trip, then Thailand
, then Belize
. Now how are your going to get your boat to all those places? If you charter, the boat is already there.
You may want to own and charter, like I do. Buy small; rent big. Have a small, simple, cheap
, easily maintained boat close to home for your between-big-trip sailing fixes.