My personal opinion, is I think people don't really need a diesel for 96% of the average towing people do, but it depends on what you want out of the truck. If you want to get the best fuel economy and ignore all the extra costs and issues of a diesel potentially having, then get a diesel. But if burning through fuel isn't a huge deal and you want a gas vehicle that is generally less complicated and potentially cheaper to maintain, then there's gas trucks that will work.
I bought my truck, a 2018 GMC Sierra 3500 Crew Cab Long Bed SLE 4x4 6.0l gasser brand new at the end of 2018 from Dave Smith in Kellogg Idaho for 41k out the door, luckily no sales tax in Montana when I was living there. MSRP was 53k, I got a good deal on it. Vehicle prices are crazy now though when for 20k with diesels you're looking at nearly 20-30 year old trucks. Anyway, I bought my truck because I was working for the carpenters union in Montana and living in my 2005 Montana 3295RK Fifth Wheel that's about 10.8k empty and 14.3k max weight, 36 foot long. So I towed that all over Montana between different jobs and usually towed it once a week to dump the tanks / get fresh water. I've towed all kinds of other trailers with it too, 14' gooseneck dump trailer, 22' equipment trailer, 3 stall horse trailer, I've rented a 40'+ duel dually axle deck over equipment twice once towed out to California and brought back 2 1997 Toyota Century's I imported, which those are heavy cars about 4,500 pounds a piece so probably pushing 15-16k pounds combined. Then I did that again down to Texas but brought back 2 smaller cars a Starlet and a Crown. I've towed a Crown from Colorado out to Virginia to trade it for my Hilux Surf and towed that back both on a Uhual car dolly, I have a 4k pound mini ex I tow around on my trailer that's probably 2-3k pounds. Towed my Surf out to Utah on that trailer for Matts Off Road Games with the Surf loaded with camping gear, my 500 pound four wheeler in the bed of the truck as well as a 108 gallon fuel transfer tank that's another 700 pounds at least. Took the 22' equipment to Arizona to pickup my first Surf I had and towed it back. Just recently my mom bought a 43.5' 2 room 2 bath fifth wheel camper in Cheyenne and I went up there to tow it back home, well I went down 25 after picking it up to Johnstown to weigh it on the scale there and then back out to Briggsdale where I live so that's probably 2 hours, truck and trailer was 21,360 on the scales, 4,180 on the steer axle, 6,100 on the rear axle, 11,080 on the trailer axles. Which is roughly 600 pounds short of my trucks max payload and it's definitely a little over the trucks max weight, truck is rated at 13,760 towing I believe, and about 3,960 max payload, still handled it fine even when the trailer brake fuse decided to blow and I had to replace that at the scales, still was able to stop everything just fine with no trailer brakes.
But the point is, I've towed a lot with my truck, I've towed thousands of pounds over what it's supposed to be able to tow over 2 of the biggest mountain ranges in the country which are the Rockies and the Sierra Nevadas, I've towed through death valley at 110+ degrees and I've towed in Montana at -30, -40 degrees. From literal coast to coast and border to border I've towed trailers. 8 years later, 100,300 miles later the only thing the truck has been to the shop for was a weird idling vibration that turned out to just need new spark plugs and they did new wires on it as well. Just towed even, I used my car dolly to tow my Cruze Diesel to the shop to get the rear bumper fixed after being rear ended. I also bought a 1973 New Holland Skid Steer that's about 4-5k pounds and I've towed that around a few times now. I keep remembering of more things I've towed, went to Washington a couple years ago to pickup my small aluminum boat and truck camper on a trailer to tow them back. Towed my mini ex and dump trailer up to Idaho Falls to do work on my grandparents house after they passed away, towed a rented 26' enclosed trailer up there and then back filled with a ton of tools, so much weight I blew 2 tires on the trailer getting back home lol, that was a fun day. I'm just rambling at this point, but yeah 100k miles since new, all over the country it tows and it tows well and it has never given me an ounce of issues, I use Amsoil in everything that is a fluid and that's the only brand I use in my truck. Sure, trans has gotten hot 220-230 climbing steep grades with heavy loads, sure I've literally gotten 3.4 MPG before trying to tow my camper 80+ MPH sometimes doing 90-100 when you gotta get somewhere for a job you get there and speed limits are 80 on Montana highways it is what it is. But the 6.0l GM Gas motor was used in everything from GM Sports cars, to Motorhomes, to the Uhaul trucks, to SUVs, to Trucks, to their Vans, to Boats, to literally whatever in some form or fashion in the last 20-30 years that engine has been known to be one of the most reliable gas motors ever built in my opinion even Scotty Kilmer praises GM HD trucks for that motor. And I can replace my entire engine for cheaper than some repair bills on modern diesel emissions systems, lol. Injectors can be thousands and thousands of dollars alone on some diesel trucks. And bonus points, the engine bay is so massive on my truck because it's meant to fit a diesel with all its garbage, that my relatively small v8 has so much room around it I swear you could rebuild the top end of my motor and never pull it out of the truck lol. And yes, going up the passes towing a decently heavy trailer I'm doing 20-25 mph behind a trucker because at 12' feet a N/A engine is losing over half its power, but that's just how physics works the truck will get you there you just have to be patient. But my truck is never the diesel on the side of the pass with the hood up because they blew an intercooler boot trying to push their truck and trailer at 70 mph up an 8% grade. But if that's you and you have to maintain the speed limit no matter the grade or what you're towing then a diesel, is probably what you need. And when considering new trucks like I was when I bought mine, I can buy a lot of fuel for the 10k+ I saved not buying a diesel. And right now Diesel is a dollar or more per gallon than gas at Costco so is there really a savings sure you get better fuel economy but also it's 30% more expensive fuel.
Anyway, as far as size of truck goes I will personally never understand anyone who buys a 3/4 ton truck. On the used market sometimes a really good deal pops up and it is what it is I get that. But if we're choosing, especially with a diesel, I would never buy anything less than a 1 ton. I see these guys with their 3/4 ton diesels with short beds with max trim package that takes away even more of their payload, A the diesel is a heavy motor that reduces your payload, and then the trim package reduces that more, and then you're already on the least capable suspension you can get with the motor on a 3/4, and then you get a short bed so it's like why even have the engine without a bed that can haul anything bigger than love seat and you'll smash your cab in with any kind of gooseneck or fifth wheel trailer anyway. The only 3/4 ton truck that makes sense is a gasser, preferably a low trim model, maybe an extended cab or single cab and with a long bed so you can actually use it as a truck. For that reason, I tell anyone no matter what you're gonna tow or do, a 1 ton long bed is the only way to go especially with a diesel but even with a gasser like myself. Because now you have a payload that can actually handle a trailer or load that might stress your engine, and you don't have to sell your truck for another one just because you bought a bigger trailer or whatever the case is. You can jump up to a dually if you want from there, they do even make dually gas trucks believe it or not, but in my experience I've never felt I've ever needed a dually that's when you start getting 18-20k+ pound range and if you were to ever do anything commercially with the truck you're almost always pass a CDL with your GCVWR (Gross Combined Vehicle Weight Rating) because any decently sized trailer pushes you and a heavy dually diesel over 26k pounds. Cause the truck is rated at like, 12-13k pounds and the trailer is 13-14k max weight and bam you're illegal, technically. My truck is a rated at like a touch under 11k pounds GVWR and with a 13.7k rated tow rating, you'd be over your tow rating before you get to a CDL, and you can get a big heavy trailer and then derate it if needed to match your trucks tow rating to stay under a CDL. But back to the point, I wouldn't advise anyone buy anything less than a 1 ton just because you'll max out the trucks payload before you max out its tow rating or what the engine was built to do, so it's a really a convo from there of a single versus a dual, and if you want a diesel for the max towing ability and power, or a gasser for a probably less complicated vehicle that any mechanic in a small town is equipped to work on. My personal opinion and I stand behind it with my own truck and 100k miles from new, is I will stress my gas engine every day of the week versus dealing with complicated diesels especially with any kind of emissions on them. The only diesel I'd own would be a pre-emissions but lets be honest, if this is a truck you want to invest in for the next 10-15-20 years Colorado loves to do whatever California does and California is already making people get rid of their old diesels whether it was built premission or not they don't care if it can't pass their smog they won't let you register it. I'm lucky to be unincorporated weld county so I can delete and do whatever I want here but without that luxury, and even here it might change, the Government can pass a law and now your truck you paid 15k for, and put 10k into to keep it running can't be registered legally and for some people that's too big of a gamble on their investment. And I'm not anti Diesel don't get me wrong my Surf is a JDM Diesel and I love that thing (although, it's having some issues and I know it's gonna cost a ton to fix because good quality diesel mechanics don't work for cheap) and I have a rare 2014 Chevy Cruze with the 2.0l turbo diesel but that car in 2014 was the most fuel efficient non hybrid car you could buy in 2014 rated at 46 MPH highway by the EPA and it's my 3rd one. But its had its check engine light on for months now because of emissions issues, my first one had emissions issues and I deleted it, and my 2nd one I bought with emissions issues because I could get a good deal and just delete it anyway, and my 3rd one now again, emissions issues, and it's 2k+ dollars in parts to delete it on a car with 8 grand at 115k miles lol. But my commute into town is 30-40 miles each way all highway and I enjoy pushing 50 mpg if I drive it nicely so there's that. But my truck has always been the 'This truck will start every morning no matter what and go anywhere in the world I could ever need it to go' vehicle and that's what it does and has always done. I'm not dealing with plugging it in every night it's cold especially in Montana where -30, -40 degrees was the lows for weeks at a time sometimes. That truck started every day all day no matter what. My Diesel Cruze has shut off randomly on very cold mornings trying to get it to idle to warm up, that's just how diesels are but then again it doesn't have any heaters or warmers to plug in so it sometimes isn't happy about that.
But anyway, people are free to do what they want I see diesel mall crawlers all the time for whatever unknown reasons they choose to do that, I think you're on a good path looking at older diesels they're generally more reliable and that's what I would buy I'm a GM guy so I'd get like an 05 Duramax I like those trucks, but when you start getting 20+ year old vehicles issues will come and keep coming and probably not stop coming and diesel mechanics are expensive. But between old vehicle problems, new vehicle emissions issues, the Government dictating what you can and can't do with your vehicle and emissions, unless I was towing 18-20k+ pounds regularly I'd avoid diesels at all costs and that's what I did personally, especially in a climate that can get cold. Even my mechanic and I go to Lundsted in Fort Collins, he told some of his commercial clients unless you're using this truck to tow everyday all day then buy a gasser because the maintenance was nickel and diming them when they have 10+ trucks running, he's like you don't need a diesel to put 5 guys in a truck and tow a trailer with concrete forms on it to a job once a month.
Anyway, seriously rant is over this time I doubt anyone will read it, but TL

R is essentially gas trucks are cheaper, easier to maintain and do just as much work towing up to the high teens.