Hoff...you gotta work out what feels best for yourself, but the "cheap" liveaboard life costs about double what you think it will because stuff happens.
BTW...you have a whack insurance co. or adjuster. The normal procedure is to get an estimate in writing and the insurance company approves and pays the yard directly in scheduled payments...generally 1/3 to start...etc.
There is no reason for you to be out of pocket anything but your deductible and whatever work is not covered by your policy.
Now get back to writin' and quitcher whinin'!! You need to make some bread!!(g)