I think when you are in that price point it really depends on you......
-Are you looking to have something with low hours, well cared for and as new as you can get? Might look at a 5-10 yr old Moomba, Supreme, Centurion
-Are you looking for the brand name and will sacrifice the cleanliness, age and how well it was cared for? It will be tough to get a Vdrive Mastercraft, Malibu, Nautique for that kind of money unless it is higher hours and maybe a bit rougher.
Just depends what you are looking for. I personally would take a clean well cared for lower hour entry level boat before I buy something that is a bit older and rougher and a big name, but that is just me. Everyone is different and value different things.
I would suggest spending some time and having it inspected so you don't end up with a money pit as well. Sounds like you are doing it right for your first time and take your time and weigh your options and you will be super happy!!!