Thanks for the advice. I'm willing to put in the work to make sure I get a quality boat that will last, but I definitely plan to use it rather than just tinker.
The trailer looks to be in fairly decent shape (the previous owner installed rear LED lights on the trailer and tossed in two spare tires to boot); though, he advised that the springs should be replaced before doing any significant mileage. I plan to rerun the wiring since it was installed outside the trailer and put a new strap on the winch since the rope is a bit worn. At some point I will repaint it and potentially change it over to a bunk, but it isn't necessary for now.
As for the boat, the carpeting will do for my current need, except for that hideous I/O on the rear seat. I noticed a few rivets at first glace that will need to be repaired, and a large dent on the bow that I believe includes a crack, but I won't be able to do a leak test for a while since winter is upon us.