Welcome aboard. Mr. Mc. Well, the first step in solving a problem is to realize you have one in the first place (rag-bag). Your wife sounds like the sane one in the family...
FIRST major question: What do we want the boat to do for us?
Do not be set or fixated on any "brand" or year of ANY vessels (yet). Be prepared to look at anything and everything. I suspect you'll find out fairly quickly what may or may not work for your particular situation given you already have some boating experience.
Walk the local docks and talk to folks who have powerboats. One of the questions might be what does the owner like and dislike about their particular vessel.
After some period of time, sit down, relax and make 2 lists (one for you and one for the admiral) noting "must haves", like to haves" and "don't wants". Don't discuss or show each other your list until finished. THEN exchange the lists and discuss. Walk the docks some more. Talk to more folks...Possibly charter a few times. Take your time, enjoy the ride.