Like anything, you get exactly what you pay for, and nothing more. Grady White boats are overbuilt fishing machines, that do tend to have some flaws but are considered the pinnacle of a production fishing machine. It's probably unlikeley that you will jump on one for your first boat, a lot of guys are bringing up crap from the states, so look out. Get a hull survey, and just be prepared how much work a boat that sells new for over 100 grand will take once it ages to the point where someone looking for a starter boat will buy it.
A Trophy, especially a newer one, is your standard walk-around fishing boat, and the ones I have seen of late are not bad for the price (Say 1990 and up). Aluminium is practicly indesctructible, but you usually sacrifice ride quality. Besides, Aluminium is expensive, if you have to ask how much, you usually are not prepared to spend what it takes to buy one.
Unless you are looking for something small, say under 20 feet, then there are only so many ways you can build a boat for ride.
For a family, I would suggest staying away from a walk around "fishing machine" as there is very little room to put the wife and kids in. Besides, what passes for a mini kitchenette/head/sleeping area is usually pretty small and spartan in an entry level walk around "fishing machine".
For a starter, something like an 18 Ft Hourston/Double Eagle are "good" small boats. Expect to pay good money for them, better to get a good simple boat then an expensive turd. And get someone who knows boats to look at one before you buy, seeing if it floats and drives only scratches the tip of the iceberg.
For safety, take a Power Squadron's course. Do everything they say.
And maybe tag along with a few experienced friends who fish, or a few trips with a guide to get the hang of boating and being on a boat before you let her rip on the water. (Lots of good guides on this site). This will establish that first off, if boating is indeed for you and your family, and give you an idea of what can happen as soon as you cast off from the dock and go, and last, but not least, show you some success so that if you run into a wall when learning to fish, you will know that there can be light at the end of the tunnel.
BTW, I have probably one of the more safe/stable fishing machines for sale, may be a big jump for a starter boat, but it's taken hundreds of my guests miles offshore and back with loads of fish.
