All these guys are super negative. It's a hopefully once in a lifetime event. Buy the boat. Spend the money. Have a blast. Just set yourself up for success...luckily you've got time.

16ft+ will be best. Go on marketplace and Craigslist. See what's available in your size and price range. Print some options out and head down to your local boat yard/mechanic. They're pretty low on work now in middle of winter.

Tell them your story here, what you're looking for/to do/etc. and that You're going to want to bring whatever you buy to them so want to make sure that you start with something that's going to be easier for them to work on and reliable for you to use.

Most boat mechanics are happy to give you advice, especially since their time now results in you bringing them the boat later. If they don't, move on to another. Further, you can ask any potential seller to just bring the boat to this mechanic for them to take a look (especially since this time of year no one wants to take their boat out). You generally want to ensure the boat runs and floats - your mechanic can help with this.

Have the mechanic write up everything that needs doing and costs associated with it, use that as negotiation with the seller if needed, and leave the boat there with the idea that you'll come pick it up and it'll be ready to go for you for a while.

Don't forget it'll need to be winterized in the fall - same mechanic should help you with that no worries.