MPM, you are getting some good advice here. If you are definitely getting a boat, there is nothing wrong with getting a 16'. Most importantly, you'll find out if you actually use the boat or not. If you do, you'll decide very quickly that you need/want something bigger. If you don't use it, and it hasn't broken down, then you can sell it and move on without much of a loss. Regardless of the boat, I think you just need to be aware of a couple of things. First, you are buying at the worst time of the year. Everything you're looking at would be $1000 cheaper if it wasn't July/August. Who wouldn't want a boat in this weather? Things feel different in the winter when the boat is taking up garage space or sitting outside getting rain and leaves on it all winter. Second, like any well used car, if the motor goes, so does the value and functionality of the boat. So, just be aware of what you'll do if the motor craps out. Fix it? Repower with new motor? Repower with used motor? Sell the boat without a motor? In any of these situations, the original math goes bad in a hurry. It is how lawn ornaments are born and marriages get ugly.

My advice would be to wait. Find something in late fall or winter that you can treat as a project (any boat you buy WILL be a project) that will be ready to go for next spring. Look at something like an Olympic or another classic NW boat with some form of canvas and windshield. Ideally, find a boat that comes with all the small stuff: safety equipment, downriggers, crab pots, etc. All that stuff adds up in a hurry. Also, make sure the trailer is in decent shape. Finally, make sure you have the time to not only use the boat but to maintain it once you get it. If it is something you are using in the salt, take 30 to 60 minutes after each trip to flush the motors and get the salt off of everything.

Good luck! My boat brings me a lot of pleasure and is one of the last things I'd want to give up but sure takes a ton of my time and money.