With putting retirement criteria on there, I will make assumption that most of the time you are talking about a fifth wheel for two people. So, first let me share my experience. I started camping with old 35' Prevost, then traded it in for 37' Cedar Creek. We have regretted getting something that big for just the two of us. Our initial thoughts were places for kids or grandkids to sleep ... rarely happens and when does we find it less enjoyable when kids are staying in RV. Most campgrounds have cabins for rent ... or carry tent & sleeping bags so everyone can have own space. Some campgrounds have restrictions regarding length or it can cut down on selection of available campsites due to length. So we are wanting to downsize. Approach we are taking is we have made list of things we definitely like and want to have and focus on it is for two of us traveling. Then get shortest 5th wheel that has the quality and features we want. Also, newer 5th wheels have front ends that are short bed friendly without slider hitch so ask about that. Slider hitches make truck beds virtually useless for anything else since they are too heavy to remove without a lot of effort and hitch basically takes all the prime space in the bed. On top of that they cost about twice what any other hitch costs. I had a slider hitch initially on my 2016 2500 and when I ordered new truck switched to Reese Goose Box on trailer and love it. This allows me to easily free up my bed while on the road when needed by simply removing hitch ball. But if I were to do over again, I would get Gen Y Executive Torsion Flex to reduce needing to keep air bag properly inflated. I would also look at MORryde IS suspension system and disk brakes. The smoother your 5th wheel rides, the better it handles and also saves on things getting broken going down the road. This option comes on some newer 5th wheels or can be ordered if ordering 5th wheel. Can also be installed after purchase by MORryde.
Also, plan for cameras on your 5th wheel. No matter what, at least opt for the rear view trailer camera option. Everyone loves how my rear view mirror displays image behind 5th wheel when it is attached and it is much more reliable than wireless cameras. Had one instance with old wireless where lost signal and when that happens video continues to show last frame. Checking side view mirror, car that was showing on rear view camera was actually beside me taught me to have no reliance on the wireless camera. Hard wired camera is simply much better. This is simple install for most part since it is a single cable that goes to back of 5th wheel and then morning camera. I mounted mine about two feet above bumper and was able to fish wire to belly.
Trailer surround video is also a RAM option that is also offered by GM and others. I was able to get cameras added to my Cedar Creek ... but when talking to new RV dealers about installing, they claim the way exterior walls are now designed, adding wiring to walls after manufacture is extremely difficult and some RV dealers will tell you they won't do it ... so if you are considering that option ... keep that in mind. At some point RV manufacturers might offer prewired for surround video like most prewire for solar. The option is a bit expensive so if you can't get installed on 5th wheel you decide on you might want to save money and not order it.
Gas vs Diesel ... go Diesel for towing ... gassers for the drag strip

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2500 vs 3500. Like I said, I had 2016 2500 Cummins and loved it. Towed Cedar Creek 75+ through Nebraska and Kansas just fine (I live around Saint Louis, son lives in Cheyenne, Wyoming and brother lives in Colorado Springs). Ride in the 2500 was a little rough at times, but wife with her back surgeries found it acceptable. That truck got t-boned by a young lady on a cell phone so ordered a 2022 3500 with HO engine and all the towing options. I do notice the difference towing with the HO engine when it comes to mountains. I also like that it changes transmission to Aisin transmission. If not considering HO engine, I would go with 2500 ... same engine, less weight, smoother ride. Note: my wife will not ride in my 3500 unless she has to and complains about rough ride every time she rides in it ... again, she has back issues so I understand.
Short bed vs long bed ... single vs dual ... my view is short bed standard. This becomes main transportation for touring and shopping while RVing and is enough of a tank. I definitely don't want anything that makes it bigger ... as a matter of fact, I really don't like that the newer ones are so much more off the ground than they were 10-15 years ago. I'm just towing stuff down the road, not 4 wheeling so I don't need all that ground clearance. Stability on the road is also governed by suspension on trailer. With suspension I have on my trailer, I have no issues with sway and have been in some pretty bad crosswinds and have not had any issues.
That pretty well covers my experience ... hope it helps.