To the topic at hand, I think that in Florida and the other southwestern parts of the country where it gets really hot, especially during the summer, there's a huge amount of CC style boats, and for good reason. I've got a 2004 Grady White 228 Seafarer, of which it is a walkaround style of boat, and love pretty much everything about it. That being said, I'm in the Seattle area where the weather is quite a bit different and the water is especially different in terms of temperature. Most of the time, the water in the Puget Sound doesn't get to be more than 48-54 degrees or so, even during the summer. So you can imagine, you'd rather keep the water, spray and elements off of you when motoring, especially if you do any sort of winter/spring/fall fishing when the weather isn't ideal. I also love the 228 Seafarer because it does have a small cabin, but I can put my downriggers in there as well as all of my other fishing gear and everything else that I might need. You can put safety gear in there like extra lifejackets, a toolbox or tool kit, etc. She has a seating for 6 and I've actually had over 10 people out on the boat before that were either seated, standing or sitting up front on the bow cushions, yet there weren't any issues at all. It really depends on your fishing needs and what you want to do with the boat as everyone uses their boats differently.
Up here, we troll for salmon and typically always fish off the stern of the boat. Some people use their boats up here for mooching or jigging, so it might make sense for them to have an open bow, but I don't ever do that kind of fishing. For someone like yourself where you've got the wife and kids and will likely use the open bow, it might be something where you consider maybe a dual console style of boat like a 275/285 Freedom? That way, you can use the open bow of the boat for cocktail cruising, yet you've got the rear of the boat to where you can do just about anything with it that you'd be able to do off of a walkaround style of boat. From a quick glance at the GW site, the 275 Freedom has an 8'6" beam which would definitely make it a bit easier to trailer as opposed to the 285 Freedom which goes up to a 9'6" beam. With twin F200's on the 275 Freedom, you're looking at a tested weight of around 8k lbs, figure another 1k lbs or so for the trailer and another potential 500 lbs for whatever other gear you might have. At likely less than a 10k lb towing weight, you've still got a good multitude of trucks that you can pick from that will be able to tow that quite reliably. In regards to a tow vehicle, my tow rig is a 2010 Toyota Tundra with the 5.7L motor and purchased a couple years ago for less than $20k as well as 120 miles , it has a 11k lb towing capacity of which it easily tows my boat.
