Hi Landlubber.....,
My 2 cents worth would be......
Try not to buy a "project" boat unless repairing, upgrading, and just working on boats is what "turns your crank". Otherwise, I know of too many people who end up regretting their purchase as they spend "bags of money" (it always costs more than you think) and/or hours and hours and hours of their time working on the boat and they don't get to use it enough!
The 2 "catch phrases"? Anytime you have to change boats, you lose (money - there may be the very odd exception but that is rare). So, best advice is to take your time now, carefully consider what you are planning on using it for (details of that - not to go boating
), and what makes and models will achieve that for your within your budget. Also remember when "boat budgeting" that you will spend more money than you think (in the vast majority of cases) after the sale to repair, catch up on maintenance, upgrade, add items, and just making the boat your own. This can really add up, so plan for it! In this way, you can stand a better chance of "getting your second boat first" (in other words getting it right 9for you)).
Size. Get the smallest boat that you will be comfortable on, that meets MOST of your needs, wants, and nice to haves, that is in the best condition possible. Remember that all boats turn out to be a compromise. It is next to impossible to get everything you want (unless you have lots of experience and knowledge, and bags of money) on any boat, but if you spend the time and energy up front, you can probably come close!
However, as Murray wisely said, don't take too long, enjoy the now! Start the process and go boating.