I would also mention that moving from a PUP to a TT we lost the feel of camping. All those issues, wet canvas, load and unload, rainy days etc. that people are glad to get rid of are indeed part of being out of doors.
The other things we had not considered until we rented a TT were, pulling in or out of gas stations, driving though city streets to find a quilt shop, a hot day with no electric make a TT a dandy oven. All of this is offset by the shear convenience of having your house and restaurant ready to go with little effort.
TT or HTT it is a big step; floor plan, tow vehicle and cost, all have to be a good fit.
Go slow and good luck.