Don't forget the most important thing: money. After you decide what you want to spend for buying and how much you can spend a month on maintenance, then you can go on the internet and see what are your choices within your budget.
Second step could be to find out what you really want to do with the family: cruising, fishing, overnights, diving etc. Based on your budget, you can choose the boats that fit your need. No boat is perfect. You will have to make compromises.
I have owned a trailer boat before and now a very small cabin cruiser. I enjoyed both.
Most trailer boats are open fishermans. You don't see too many cabin cruisers pulled on the road. The main reason is weight. A 25 footer weighs over 5,000#. You add gear, gas and the weight of the trailer and you are about at your limit. I would avoid towing the maximum capacity. Launching and recovering boats over 5,000# is not fun. At least, not fun after a while.
If you want to trail and have a great time, keeping your boat at home, it would be preferable to have something light. After all, outboards are cheaper and easier to maintain. If you want a cruiser, factor in marina costs.
As for courses, I would suggest you take the course before buying the boat. The Auxiliary Coast Guard or the Power Squadron offer great classes. At least take the safety class which last only one full day.
Also, buy yourself a Chapman book.