Agree with keep what you have - 100%. I just spent the last 10 years in Colorado's, last one for 8 years a 2018 long bed V6 / 8spd 4x4, lifted 2". Tow rating is 7000, payload is 1550 which isn't bad. I towed a 5-6Klb car trailer quite a lot including long distance trips over significant mountain ranges. The small truck did great for a small truck, but it did make for a more stressful drive every time. I used a wt. dist hitch always. My trailer tracks really well - it's a very nice trailer and open car trailers are reasonably aerodynamic which helps too. So it was adeqate. But I was always alone in the truck - if I had passengers and cargo it would have blown up the GVWR for sure - I was near the limit on everything.
The biggest issue I had was power, and since I moved to CO last year it's a real problem in the mountains around here - the poor V6 is ripping along at 6Krpm trying to maintain 45mph up the steep grades on I70. And there isn't much margin there. So while it's workable and technically within the limits of the truck, it's not ideal.
I have had larger trucks including 2500 suburbans so I have a good feeling for the difference. Never really owned a 1500, but had a Nissan Titan but that thing was a beast and closer to a 2500 in ratings.
I just traded in the Colorado for a new 2500HD 6.6L. This thing is a serious truck - it will tow my rig with ease. And it does give me the opportunity to consider getting a travel trailer down the road. No reason for a 3500 in my case and my kids are grown so if we did get a travel trailer it would just be for 2 of us so don't have to go nuts there at all. Anyway - just went the other direction as what you are considering and so far I wouldn't look back on my move. 3 days a week 50miles RT I would just drive it - maybe it depends where you live but assuming gas prices get back to where they were or close - we get gas for $2.5 a gallon in CO so 150miles a week or aprox 7K miles a year considering vacation weeks, etc. doesn't seem like much of an issue to me. It's not my only vehicle in my case - I have two Camaros so if it were me I would drive the 2016 all summer and the truck all winter and no biggie. How bad is the mpg on these things anyway? I would think it can pull 17 on the highway? That's not terrible at $3 / gallon.