CaptSydor,
Our equipment choice was dictated by priorities.
#1. Budget limitations - we could not buy that 5er with garage and the big TV. We also did not want that big of a footprint.
#2. Our biking. We ride. It is what we do. We travel with five bikes - a tandem, 2 road bikes and 2 mtb bikes. The bikes had to be in the truck under a topper; not outside on fr. or rear hitch racks and not on a roof rack. (CaptSydor - you know why! Been there done that). That meant a long bed pickup (tandem!).
#3. The trailer had to fit our budget and the trailer had to be suitable for our multi-month trips. We spend 7 mos. per year in a 26 TT in the SW. No dogs, no kids. Camp locations are always chosen to maximize % sun and good riding opportunities. We have found that our 26 ft. trailer works well for us but we are literally outside from AM to PM. It works for us. We have no interest in going larger.
Our setup requires thoughtful packing and limitations on "necessities". We are OK with that. We are also OK with the reality that sometimes things are a little tedious - like when we are on the road and we have to unload three bikes to get to the two in the back of the bed that we want to ride that day! That "dance" is part of the deal when you have decided to protect your "tools".
PM me if you want. Best of luck in the process and ride safe.
DB2