I have towed a number of flat, storage, and toy hauler trailers over the years with my half ton Silverado and Tahoe however none were longer than approx. 20 ft.
We are now retired and are really geeked about starting a more "mobile" lifestyle. It will be part time at first but we also plan on mostly extended stays either up north or in the south during winter and don't want the walls to start closing in.
Considering price, amenities, that I usually lease, etc. we have decided that a TT will be our best "bang for the buck" option and of course, she has determined that the one that will "work" for her is the Jayco 338RETS which is a monster to me at almost 40 ft. A large wardrobe, shower, and living area are most important over the number it can sleep because it will be just us 2 and the dog almost all of the time.
I know I will have to upgrade to at least a 2500hd. But I am also not sure about a diesel over a gas engine because our usage of the trailer will at least in the short term, be sitting on property up north for the summer and us driving up for a number of extended weekend stays, and then most likely towed to Florida or Arizona during the winter. There may be a few other occasional trips elsewhere, but the truck would mostly be used as a daily driver the vast majority of the time which to me says a gas, single rear tire version is the best option.
But with all that said, the main concern for me (not her) is pulling/maneuvering a 39+ ft trailer, especially after viewing the 338RETS thread which had pictures of one being opened like a can of sardines!
So, given that I want to limit my new truck to a 2500hd gas version, and have never pulled anything quite that long, would you recommend it anyway or should I try to talk her down off of that large of a trailer? And if so, any suggestions/ideas that might help sway her to downsize? Once she sets her mind on something.............