a good book for beginners that dont really know too much about it or the lingo is "sailing for dummies"... it is NOT a book for idiots, but is simple to understand as its written for people like yourself who want to learn, yet dont know the lingo or where to begin. it helps teach you all this.
im not even sure you really know what you really want to do with a sailboat except have fun..... if you get one too big, it may not be as much fun as a smaller one for first time owner who actually wants to sail.... get one too small and its like dinghy sailing.
a "fixer upper" is exactly that and will take lots of TLC (Time, Labor, Cash) to make it what you want. (they are a bit cheaper to buy, but can be more expensive to own)
a turn key, ready-to-sail boat is a good choice, as if you decide you dont like boat ownership, you can probably sell it and recoup most of your money after a year or two,
if you keep up with the general maintenance of it.
bigger will give you more room inside, but its harder to trailer, more expensive to keep on the water (dock fees) and may be a bit harder to sail single handed, meaning by yourself and without a crewmember to help.
a smaller boat usually has lighter sails which are much easier to handle, usually more simply rigged so single handing is much easier... all things being equal, the maintenance costs are cheaper than they are on a bigger boat that may have more systems.
my suggestion is to read a couple of books sailing for dummies, then step up to the annapolis book of sailing... go online
here.... or
here is something a bit more basic. do a search for anything or any term that you dont understand, and it will be there on your screen.
almost everyone you talk to will say that when they owned a smaller boat they sailed it more often, and that it can be more fun than a bigger boat. but its all relative... some people like to sail and cant really tell the difference between discomfort and adventure, and yet others like the comforts that a large, roomy boat can offer, but may not get out sailing as often as the small boat sailor... and there is everything in between, and the extremes at either end. we cant tell you "who or what" you are as a sailor, or who or what you will become, but it is
my opinion that starting simple is the very best way to get the most fun out of the learning process when you are teaching yourself as you go.
in your position (and i once was, except that I had never stepped foot aboard a sailboat), i would purchase an affordable smaller boat, a 21 or 22ftr in sail ready condition and have a blast while learning more about how things work... then as you get into the sport more while being a boat owner (being a boat owner gives you a much different perspective that being a crewmember does) you will then learn what you actually want to do and which direction you want to go.... so when you buy your second boat (and you will) you will be able to get what you want, because by then you will be experienced enough to KNOW what you want.
for someone who actually knows they dont know, and havent spent enough time around boats to know the maintenance required and all that can go wrong that costs money, I would NEVER suggest getting a boat that is NOT easily trailered, as their first boat. unless money is no object, then the game changes

