Living aboard is quite fantastic, but it does have a learning curve. You will find great spots just by getting out and throwing the hook. Looking at charts to find good anchorages is the best way to go about it. Buy a chart book for your local area, and the areas you wish to be. You will need them anyways. I don't know how much boat experience you have, but "free" boats usually cost more then a decent used boat off someone who is in a pinch. To have a safe vessel is critical, and the less things you need to fix, the cheaper the overall cost is going to be. I always tell people to get a functioning 25 to 28 ft boat for less then $3k that is a working fixer upper with some decent equipment to learn about boats and if the life style suits them, and if the glove fits find a nice 30 ft to buy or rebuild. You can save a lot of money by keeping the equipment from your first boat, and buying your second boat with less or no gear. Typically your first boat is not your ideal boat. After being out on the water for a year you will learn what is actually important for you to have, and what is just a waste of space. You don't want to go through all the work and money putting a boat together to discover it is not really suited for your intended purposes. The best way to learn about boats is to just get out on the water and deal with the circumstances, just don't be a fool and kill yourself.