The best way to transition into being a liveaboard is the Band-Aid method...
Just do it, set a goal, set a date and make it happen.
We made the decision to liveaboard, having never owned or sailed a boat before. We put the house up for sale, started getting rid of our "stuff", ignored all of the nay-sayers and made it happen.
We finally sold the house... within a couple of weeks we were living on our very own sailboat. We havent looked back and have ZERO regrets.
Dont make excuses, make it happen.