Your signature mentions kids -- how old are they? Are they happy sitting for days on end in a moving vehicle? (Some are. Mine were not.)
But you are not crazy. We have taken trips in that general area lasting six weeks --- without the kids (who are now grown). And if you take a few shorter trips before the Big One, you will be ready for the long haul, so to speak.
My only advice would be to avoid days that are much longer than 300 miles. Towing is hard work, at least from the standpoint of mental effort. Since a vehicle plus trailer is so much more cumbersome than a lone vehicle, you have to drive even farther ahead, with even greater caution than usual. It is tiring after six or eight hours on the road.
I am not complaining -- we really love trailering! But it is not effortless.
