Single person - How difficult to do everything by yourself?

I can only answer about the MH/toad scenario. Given reasonable quality equipment, it is SUPER easy. My Newmar Dutch Star required me to push FIVE buttons to setup (level & four slides). Of course, I still had to connect shore power/water if at a campground. A toad is very easy to connect/disconnect with a good tow bar - it does not require level, straight, or even the 'perfect' distance (two pins, two safety cables, and the electrical plug).