Jl,
I liked what Jackdaw & Shemander said. So for the sake of taking a neutral standpoint, here are some of my thoughts.
I used to use my girlfriend's father's boat back in the day. For the length, he lived aboard for 12 years. Yea it's doable to live on but, he was an old salt & used to living a Spartan-like life. He eventually moved up to a 44 footer for better live aboard space. He said he hated the clutter.
So, let's get to your question, what type of living are you used to, a 1 or 2 bedroom? Space is at a premium for live-a-boards. If you have alot of clothes, electronics, & misc. things you are used to surround yourself, I assure you this will become a culture shock. Smaller sailboats as in the 30 ft. range are cramped to begin with, ya can't move your house or apartment into the boat, as It will NOT fit.
So, you need to make the decision,. Will I be happy giving up most of my worldly possessions to live aboard? If you can answer yes to this, maybe living aboard is not a bad choice, then again. Just remember to look at it objectively first, to get the best answer in your choices.
Living on the hook presents its own inherent problems. If at a dock, life is easier. One thing I have seen over the years are, that many move to living aboard do less sailing.
It's only my thoughts but, it's your call pal. Just make sure you think it thru wisely.
CR