We went from a Monaco DP to a Open Range 216. The jury is still out on if it was a good decision or not. When we had the MH we pulled a Jeep Wrangler. I could hook and unhook the Wrangler in less than a minute. Backing up was never an issue. Seems like a whole lot more work hooking and unhooking the TT. I'm assuming that it'll get easier as I become more used to it.
I miss the cargo and storage capacity of the MH. I basically had a basement the same size as the motorhome and 4' tall. With the TT I only have the pass thru in the front under the bed. Of course the TT is smaller inside but not by much and that isn't an issue since there's only the two of us. The MH could carry tons (literally) of stuff without any concern of being overloaded. The TT not so much.
With the MH cross winds were never a consideration but they do come into play with the TT. I really miss my generator and arriving with the RV already cooled down or heated up has it's advantages. Also, when overnighting (yes, at WalMart) I never even had to get out of the MH.
MH carried 100 gallons of water, had 40 gallon black tank and 70 gallon gray tank. TT is smaller and I seem to have to try to keep the tanks as empty as possible to keep the weight down. On the DP I got 11 MPG. With the TT I average about 8.5 on the Armada.
I'm not making any predictions right now and will give the TT more time but if I had it to do over I'd probably hang on to the MH.