I want to consider various options. Liveaboard/Cruising is one of them. Oh, I'm a neophyte at best.
I lived in then Twin Cities for 28 years. The fact that you did something for a long time is no reason to be tied to thinking you could not do something else. The better question is if a change in lifestyle will be better for you or not. A change in lifestyle is not assured to be "better" but it clearly would be different. You can change the place you are and the way you do things easily. It's not easy to change the fundemental parts
of who you are and not a requirement either.
I would not look at crusing as only a lifestyle. It can be something you do from time time or in many ways different from others. It would proably help to not look at your life as chapters because it makes the assumption that everything prior was not at all related to what you do next or even important. You could change the geographay without changing yourself. Being on a boat wouldn't make you more or less who you are just where you do it.
You would need to learn some new tricks and that can't be a bad idea as far as learning
something new is a part [art of growing. New things bring new excitement, but bringing some of the old things forward makes for continuity. You need some of both to make it to the next chapter. It's about finding the way that works for you. It may make not sense to anyone except yourself but if you use a boat we all sure would love to hear about it. You can find about 100 different ways to go about a it. Many of them are written about it here but we get new ideas all the time.