Nate since your wife is going to be the deciding factor on whether you get a truck....and what size, I think I would get her feelings on what she will or won't accept in truck size. When you go to look at the HDs she may just say no, but let's hope not. She may say a 3/4 is as big as she wants (remember there is virtually no difference in a 3/4 and 1 ton except additional payload for towing). With that in mind get her take on what kind of truck you both want.
Some thoughts on that; start with some well equipped HD trucks - they make trucks as nice (or nicer) than luxury cars IMO. Don't test drive a 1/2 ton first. They DO ride softer but give away a lot in towing ability. Have her note the increased visibility (my wife loves it, my daughter says she thinks she's in a semi).
Initially your thought was maybe a 150 and a 250 was overkill. If going with a 250 might as well go with a 350/3500 if going to the HD truck - if DW will go for that. Once that decision is made, get the payloads (from the sticker) of any prospective truck and that will then give you a baseline for what size trailer will fit. You started off with a very small trailer choice so going to any HD will open that up a LOT and you should find something you both like and still be well under payload of anything (HD) you look at. There would be no need to go look at top end luxury 20k 5th wheels (and spoil looking at the rest) if all she wants is a 3/4 ton.
Also (I know you know this) as the size of truck and trailer expands so does the cost. Keep that in mind as you start browsing. If you settle on a big HD truck it's very easy to let your eyes/wants get carried away; as I used to tell my DS a long time ago; "don't let your alligator mouth overload your hummingbird a??". Good luck finding the perfect match and keep us informed.
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Danny and Susan, wife of 56 years
2019 Ram 3500 Laramie CC SWB SB 6.4 4x4 4.10
2020 Montana High Country 331RL
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