This thread has provided some valuable information, so thank you for all those who contributed.
A little background on myself as well. I'm 32, with a wife and two kids. A 4 year old boy and a 10 month old girl, the last thing I want to do is put them in danger. The plan, as it were, was to buy a decently sized TT and park it down at a campground at the ocean for beach season, May-October. With maybe one or two trips up north in the Spring/Fall. We wanted to get a bigger trailer so we could have another family with us at the beach.
I'm definitely doing my homework on this, which is why I asked for input. I do have the tow mirrors, integrated brake controller, the whole nine. I custom ordered this truck to tow (outside of ordering a 2500, that is).
It's about a three hour drive from my house to the ocean, though, I suspect with a trailer it would be more like 4.5 to 5.
I was planning on several short trips in the immediate vicinity to get comfortable behind the wheel.
I think I am going to try to stick to something around 30' if I can find it, I think going slow and having the right set up I should be okay.