Selecting a live-aboard cruising boat, is by it's nature a subjective process. General coarse metrics can be universally applied but the ultimate metric is whether the boat allows you the most flexibility to go where you intend with options to change your mind, in the comfort and life style you desire. I am a pragmatic cruiser, so easy and complete access to all systems is essential. I was advised when I started cruising by an old salt "...sonny don't forget everything on a boat be broken, ya just don't know it yet..."! Access produces dividends via prevention and time$$$ saved for repairs and the eventual system replacement when paying by the hour for marine technician labor.
Air draft and in water draft can severely limit or facilitate where you can go and anchor. Getting onto and off the boat is something you will do repeatedly. Can you easily get on and off the boat safely? How about carrying a dog, groceries and parts. Have a bad back or knee/hip. Orthopedic injuries don't get better with age. How about getting into or out of a dinghy? A boats ability to cross oceans is often overblown as is seldom done by most boaters and alternative options such as shipping are always available. I personally like the comfort afforded by truly redundant twins with separate running gears that actually cruise the boat near normal cruise speed and still enable handling. Tanks that won't corrode(e.g. fiberglass) are a real plus in the out years resell values. Storage is another. You will fill it and need it. All that said, I am a huge fan of the Great Harbour Trawlers especially the N's (My favorite, however I am prejudiced as I formally owned one and cruised it 44,000+ miles. They have proven open water cruising histories(one went to Hawaii, another to Bermuda from Jacksonville Fa.) and are unmatched by interior space within their 37'X15'11" foot print. Lot's to think about good luck, stay safe and Healthy.