I think there have been some great responses so far.
@Tally Ho put up a solid list and
@gulfcoastsailor asked great questions which will help you refine your search.
I have a couple of questions too.
Define cruising. I could go to the marina and ask 10 people and get 10 different answers. On the Chesapeake Bay quick answers would be day cruising, over night cruises, Annapolis and back, sightseeing, coastal or blue water.
Live aboard..... It has a nice ring to it. That said, it is not a small home, an apartment, or a tiny home. It is back to my navy days where everything I own fits into a seabag, a suit bag and a shower kit. Food and potable water storage is not much better. Speaking of potable water, if storage is limited do you intend to make it? Does your price include a water maker?
With slips becoming tough to find, will you rent one for your homeport? Do you attend moor or anchor? A slip allows for comfort features, water electricity, a parking place. In my marina fees are higher for live aboard. In Virginia electricity is higher if you do not live aboard. If you moor or anchor does your cost realistically include a dingy? Is there a way to safe guard your dingy when you do go ashore? That is a question for cruising too, the world is full of pirates, scoundrels, scallywags and idiots. Example, our marina has a restaurant. My best friend caught a family letting their children board, tour and play on boats at the marina while they waited on a table.
If you do rent a slip as a homeport are you budgeting to keep it while cruise? Or, find a new one when you get back?
My suggestion, by a starter sailboat. Learn to sail. Hang out listen to sea stories and tall tales, and figure what is really on your heart.
Good luck and peace be with you.
PS I just read this update
Yes, it is an emotional roller coaster for sure. All your questions are great and depending on my emotional state at the time of consideration, I have answers for them all. But as I view boat after boat and consider the reality of everything it does cause me to hesitate. And then there's the money thing, that everyone is telling me is very low for a real chance of achieving what I want ????
after reading it, I am doubling down on my suggestion.
My suggestion, by a starter sailboat. Learn to sail. Hang out listen to sea stories and tall tales, and figure what is really on your heart.
Good luck and peace be with you.