This thread is for newbies. I was just sitting on the bow this evening looking at the sunset and smelling the shishkabobs on the grill thinking just how good we have it. Granted it is only about 60 degrees fahrenheit right now here in Boot Key Harbor (Marathon Florida), but it is the middle of winter. A cold front has come in but it will be back up to 80 on Tuesday. Looking out over the harbor and seeing all the boats against the sunset is a beautiful feeling. We have been living aboard and cruising for about 4 1/2 years now. My only regret is that we did not do it sooner.
Newbies I know it is hard to sell the house and a lifetime of possessions, but I assure you it is worth the pain in the end. I would pass on the advise we received. Go small, go now. Buy the smallest boat you can be comfortable on, not the largest and best that you can afford. It is not a house or an investment. It is a vessel to take you to your own paradise, whether that paradise is the Bahamas, the Keys, the iCW, or wherever makes you happy. There is no one place that is everyone's paradise. It is different for everyone.
Do not let ANYONE tell you this is the way you do it. It is different for everyone. The way that makes YOU happy is the right way for YOU. We started out for the first 1 1/2 years on a 25' sailboat and we loved it, but as time went along we learned about trawlers and we came over to the dark side. We were happy on the small boat and we are happy on the "big" boat. The point is find your own way. This and other forums are a great source of knowledge and inspiration, but take everything with a grain of salt and find your own path.
Perhaps others can give their advise as well. By the way take everything I just said with a grain of salt as well.