You have the understand how big a role "stuff" plays in your life. "Stuff", as opposed to provisions, tools, and essentials, is endemic in most lives, and can drive a number of curious boating decisions. In the book "Sell Up and Sail", Bill and Laurel Cooper indicate somewhat contra-intuitively that their age and Laurel's need to cart around a one-tonne library (literally, apparently...we are talking thousands of books) drove them to purchase a 65 foot Dutch sailing barge!
At the other end of the scale, there are people quite happily living on Contessa 26s. Not many, though...you are more or less at the level of permanent camping at that point.
Investigation of how others have done it can not only help you decide if it is for you, but can also determine if you're doing it the best way (or in the appropriate boat) for yourself. One tactic is NOT to sell the house, but to rent it out for a winter, and to live aboard in the worst local conditions you can anticipate. Get through that cheerfully, and you'll have a lot of your questions answered. Hate it, and you won't have radically altered your circumstances.