I went from a 14' Grady White Lapstrake
to a 1967 16'7" Boston Whaler
to a 1975 22' Mako (I gutted it and rebuilt the deck/transom, etc.)
to a 2007 240 Everglades (now called the 250)
- this is my actual vessel -
View: https://www.youtube.com/watch?v=RMlCACo1WcM
Each time I buy, it is during a downturn in the economy. Too many buy boats on credit. Worst possible choice! I bought my Everglades for 40 cents on the dollar in Key Largo (as a repo) in 2010. Boat still runs flawlessly. Arguably the best CC Boat made. It's a Tank!! A Bob Dougherty boat (of Boston Whaler and Edgewater fame).
(Albeit I do like Regulators, as they are the 2nd heaviest boat in their class behind Everglades).
Keep in mind that if you buy an older (pre-2005ish) fiberglass boat, almost all have marine plywood in the deck and most importantly in the transom. & many transoms are soggy moosh and their owners don't even know it. Bring a hammer and do a tap test on the Transom.
Also, if you can reach any 2 part foam that has been used between the inner shell and outer hull, press it. If it is wet like a sponge, it is useless.
If you can wait for the next downturn in the economy, boats are the 1st value items to drop dramatically in price as people scramble to save their over-mortgaged and now undervalued Real Estate.