As With most things in life, living aboard is a question of balance; regrets/rewards.
For me,
Regrets; none so far, other than maybe having not done it sooner.
However, a close runner up to regrets, “reality bites” should also be a serious consideration.
How often, will in reality, will you be able to take your boat/home out of her slip. Quite often, it's a pretty major effort for a liveaboard to take the boat out just for an afternoon cruise. Most of the time it requires securing your boat so that if you take a wave/wake, your "home" below doesn't go flying all over the cabin/galley/staterooms. If you’re not going out for a least a day or two, it’s usually more effort than it’s worth. I suspect that after some time, a lot of liveaboards are disappointed with the amount of time they actually get their boats out "on the water".
Also, living aboard involves a lot of hard work, bumps and bruises. Unless you can buy a “newer” boat, there will always be something that needs fixin’, sometimes major, sometimes minor. Your first inclination will be to try to fix it yourself (hence the bumps and bruises). Depending on your comfort level of the project it can be quite frustrating or quite rewarding. But it’s how you will learn the important systems of your “baby”.
Living aboard also requires lots of hoops to jump through logistically.
The flip side of regrets; REWARDS
Like today, being down in the engine room all day and coming up to a beautiful Indian Summer evening.
And having the marina pretty much to yourself to enjoy the peace and quiet.
Also, the comfort of knowing that you’re satisfied with your boat /home with the way it is (for now) and that she’s ready to go cruising. Once you get bitten by the cruising bug, you will most likely start planning your next “voyage” as soon as you get back (if indeed you do come back). The planning is part of the fun.
As far as being a “vagabond”, well, can’t help you there. I’m going to the Keys/Bahamas for 7 months just cruising around and island hopping, mostly just diving and fishing. No set itinerary or schedule, just rough dates. I’ll be anchoring out most of the time, yet I don’t consider myself a "vagabond". Unless you mean full time cruisers, or serious long term travelers like Mr. Larry M of Hobo and others, I don't think we have any real "vagabonds' here.
As for marital bliss, the couple that lives aboard in the slip next to me have their good and bad days with some rather “loud” exchanges on their bad days, but no more so than the folks that lived next door to me on terra firma. They've been liveaboard full time cruisers for three years and are just stopping here for medical reasons.
Living on a boat would be a major change in lifestyle for most folks, and it’s not for everyone. Think of how many boats are in your marina, and how many of them are liveaboards, that is if your marina even allows them.
There is really only one way to find out if it’s suitable for you. KJ
Indian Summer evening