I am in a similar boat (pun intended) My son is in 8th. grade and I am looking at a 5-year timeframe until I can devote much more time to sailing and cruising.
I was looking for "the boat" in the same range as you. (Well actually 35-40' range) I just recently bought an old Pearson 30. It's a bit smaller than I wanted... It's not exactly a blue water boat, but I could take it to Canada, the Bahamas and down into the Caribbean. I decided to spend less now on the boat, less on maintenance, on dockage and winter storage, etc.
I will sail it here in LIS. Daysails, weekends, 1-week cruises. I will teach my son how to sail and revisit all the local anchorages... Then in 5 years I may get a bigger boat or I may just go with what I've got.