Just to throw out some info to clutter things up.
My current tow rig is a 99 Freightliner, double bunk sleeper with 12.7 Detroit and a flatbed. We are in a similar situation. I prefer to take both rigs when we wheel, as my wife is a better driver than passenger. Some times we are just going for a weekend, sometimes a week. Sometimes its just me. If its just me, I load the single rig on the flatbed, and sleep in the sleeper. If there are two of us for a weekend, I'll take my gooseneck with both rigs, and sleep in the truck. If I am going for more than a couple days, I will load both rigs in my toyhauler. Toyhauler is a converted 53' semi trailer. 21' LQ, 32' garage. The trailer is 9' interior height, and 102 width. I have also pulled an enclosed BP behind it on occassion. (bumper pull trailers behind an HDT without a cushioned hitch tend to take a beating, especially on the frame/hitch)
For me, this is the best all around option. With the bunk beds in the sleeper, we can sleep 3 semi-comfortably (fine for a weekend trip). For a week out (Trail Hero for example), completely off grid, the semi trailer is perfect. Has plenty of room for the 2 rigs, an enclosed garage in case we need to get out of the rain or cold, can sleep an additional 4-6 people in the garage if its a big group, plus it has the generator/welder/air/tools/spares/etc. Other than the time/money to build it out, this setup was by far cheaper than any other option I had at the time.
My overall length is 72' @ 13.9 height.