How Early is TOO Early to Live Aboard?

[VERTIGO]

I am finding it hard to wait till I am fully retired to purchase. I have just less than eight years to go, my situation is this: Boat I would be going after is a 44 Lagoon Owners Version.
Currently stationed in Japan, have about 2 ½ years to go here, on my return I will be debt free with around $100,000 in the bank, house will be paid off, $235,000 with a continuing income around $70,000/year. 5 years till retirement. It is myself, wife and one son who will be 10 at that time. Not to spew all my financials out but 80% of post I read with Q’s ask for more details.
So my thing is I could purchase 3-4 years out from retirement and be stationed in a place with live aboard facilities, but land life would have to go on. To include son’s school, wife’s job as well as mine. I know many have put down how expensive it is to maintain a boat, but I did the figures on my house and find that I have averaged $10,000/ year doing stuff at the house already, it just never seems to stop there as well, I live at Home Depot. My wife has already agreed to go live aboard at the 1 year out mark and live on the dock.
So I am torn between would the boat be in better shape if I were to take care of it on the dock myself for that 3-4 years, thinking of all the little goodies I could do to it over that time. I would be able to sail all weekends, to include many 4 day weekends, also 30 days a year vacation.
For those of you that have stayed in a marina long term, does it get “old” is going out on weekends and so forth good enough to justify full time living. If on a dock are you really giving up that much? The 44 sure looks like an apartment to me. I really do not want to sour my family on boat living before we start the full time cruising.
My intention is to buy used, pay cash. We go boating every weekend now, pull on the beach, grill and hang out with friends and the entire family loves it. It is only a 23’ powerboat so nothing like I am thinking about doing.
Should I plunge or wait?? I know it will be just opinions but I find many on here to be very good ones.