Sail a little , work a little , sell boat , work a lot , work somemore , skrimp save plot and plan , work more , find bluewater boat , prep boat , prep self , prep funds to cruise ( means work ). Go cruise . Come back and repeat as needed.
My wife and I took some time off from cruising to have our first kid then number two came along , we sold our boat and moved closer to the inlaws for a few years to help out with the babies . Its a break we both knew we would have to take from the water. However we know we will be back cruising again someday soon. Maybe not as soon as we want to but when we are ready . Thoughts like homeschooling have been discussed and traveling jobs have been discussed. The hard part for us is not buying the next boat too soon. My wife almost jumped on a very nice Tayana last year and I was the voice of reason and talked her out of it . This year I seem to be the one with the bug and have been looking at Tartans in earnest. She has been reeling me in from buying the next boat too soon . It all boils down to timing.
If we wait a little longer our cruising days will be better we will have more boat more money and more time to enjoy it. The biggest peave I had last time we lived aboard was having to be at a certain place at a certain time (for work) and having to bypass places you wanted to go because you had to be somewhare by a certain time. Next time we go away from land I dont want to come back till I choose to . So we work , plot , plan ,skrimp ,save and look for the next boat but we are trying to be cautious this time around because we know what we want to do and what kind of boat we need to do it . We still sail on a daysailor , cant be completely removed from sailing that would suck . But the next cruiser will have to wait .
Now to answer your question " How do you upgrade when your sailing not working ?" I dont have the foggiest idea but when you find out let me know.
Best of luck
Its hard trying to nap with that bilge pump alarm going off all the time