First and foremost, B.O.A.T. is a acronym. Break Out Another Thousand. And is defined as, a hole in the water, into which much money is poured.
That's said, I bought my first boat when I was 11 and have never not owned one.
A lot of people love the Whaler and McKee Crafts. I'm not one of them. I had a 13' McKee with a 50hp Evinrude for a couple of years, not my favorite boat. There are much better riding hulls out there. They are durable, but they will beat you to death and they can be a very wet ride.
Carolina Skiffs are going to have the same problem. If there is any chop it's going to be uncomfortable.
For cruising, I prefer a V hull. My current weapon of choice is a 1996 Key West 1720DC with a 1996 Yamaha 90. It's a great cruising boat. Reasonably fuel efficient, fast enough to ski or tube behind and large enough to keep you dry when the waves pick up.
Not my boat, but same hull.
If you plan to do as much fishing as cruising, I'd go with the center console rather than the dual console. Like this.
Engines can be very reliable. Mine is a 96 Yamaha 2 stroke, that still runs like new. It's spent it's entire life in salt water and still looks pretty new as well. Care is everything. It gets a through cleaning every time it comes out of the water. It also get the carbs run dry every trip, so there is so alcohol fuel sitting in them to attract moisture. I baby it for the most part, because I know how expensive it is to fix. While I would love a 4 stroke, they are still too expensive for me.
Trailers are usually a basket case on a used boat. Nobody seems to take care of them. I'd plan on spending some money there on springs, shackles and lights. If you put over in salt water a lot, either learn to do it without getting the trailer wet or plan on working on it every couple of years. My trailer is a 96, but I don't get anything but the tires wet launching and loading. It still rusts, but not as fast.
I don't recommend buying a project boat or engine unless you seriously want a project. It's not a way to save money. They can be much more expensive than you think. Outboard parts are priced like Porsche parts and anytime you add the word Marine on a part, the price quadruples.
The best way I know to determine how well a engine is cared for is corrosion in transom bracket and paint on the foot.
Foot paint, as a rule is extremely durable. Some loss of paint on the skeg is normal, everybody runs aground at some point.
This engine has been abused. Not only is the paint worn off the skeg, it's worn off the entire front of the gear case. That's a sure sign of repeated high speed grounding. Anyone that abuses a $3000 lower unit like this, probably doesn't take care of any other part of the boat either. I'd put it on the do not buy list.
The next two pictures are a transom bracket and steering bracket. If they look like this, it wasn't cleaned well after using and the water passages in the engine don't look much better. I'd put it on the do not buy list.
This is just under the powerhead. The entire engine pivots on this part. It is a nightmare to replace.
This is the trim and tilt assembly. It is under the engine and is visible when the engine is tilted up. Some corrosion is normal, but not this much. Another sign of not cleaning after use.
That's all I got at the moment. Hopefully it was worth reading.