..... tire upgrade ? ... etc ??

27 views and no ?

OF COURSE it would have a 5.7 !

what kind of truck ?
what kind of trailer ?

And:
How far?
How often?
What is on or in the trailer?
Trailer weight loaded?

The short answer is turn the 1500 into a 2500 or better yet, a 3500. Gene

I towed my 24' and 29' enclosed trailer with my 2000 Ram 1500 4x4 5.9 gas and it was adequate. If you are talking a modern Ram, there is absolutely no issue towing a 24' nowadays, it will be more than adequate. Check out the specs, they tow almost twice as much weight as the old trucks...

I tow a 23 ft. trailer with my 1500 that is 6,400 lbs. and 750 of that is tongue weight. I added air bags to the factory coil springs and only run 25 lbs. in them to get the truck to come up a couple of inches where I want it. The 1500 is actually rated at slightly over 3/4 ton and other than having the trailer / tow package that came with my truck, I've added nothing else. The trailer of course had anti-sway / weight distribution bars. Prior to adding the air bags, my truck was sitting next to a 2500 that was connected to a trailer of the same size and type and that truck was down in the back end the same as mine.

- EM

Although the 1500 as stated above is capable (spec wise) it will depend on the amount of use. Towing a trailer stress's the frame more than not towing a trailer - obviously, so a 1500 frame being less robust than a 2500/3500, the number of miles annually you plan to tow should be your guide (more miles more truck). Additionally power to go is one thing, power to stop is another and the ability of the truck controlling the trailer improves with truck size. With a 1500 your approaching a Tail wagging the Dog scenario on the bad end of the spectrum. Meaning, few if any enclosed trailer loaded weigh lees than the truck pulling them. As the truck capabilities increase so does the sub systems like tires, Wheels, U-joints, transmissions, rear ends. For instance, a dually pulling a 24ft trailer is much easier on everything (truck and driver) than even a 2500 and especially a 1500. But a 3500 dually is not practical for most people. When you go into a curve with a dually it is a much more comfortable feeling than a single rear wheel truck. Aggravate that with a tire typically found on a 1500 and it gets worse. I'm not saying get a 3500 I'm saying think about what your really going to be doing, short trips 25-30 mi a weekend a 1500 should be fine. Traveling 100's of miles regularly get a bigger truck or smaller trailer and enjoy the trip.
As support of my thoughts I've towed using a bunch of methods - Tow bared my first race truck from Roch NY to Reading Pa -320mi, with a /6 stick Van (read as Young and dumb), upgraded to a 21'open trailer and a "Job rated" D150. A D300 Ramp truck, D350 and 3500 and a 36" Enclosed Gooseneck and Now a 3500 and 53' Gooseneck. Of all of those combinations the 3500 and 36' goose was the best (all things considered). I am now in the midst of getting a bigger truck, The 3500 pulls the 53" but very close to the "Tail Wagging the Dog" scenario I spoke of prior. There's my make of it what you will.

couple things Doc
For towing I would rather have short wall 20" tires than 17" with a tall sidewall.
See if you can find performance friction brand pads for your truck.
Good shocks like Bilstiens would be good. Air bags in back would be a big plus.
If you haven't bought the truck already, the longer the wheelbase the more stable it will be towing.

I tow a 16 foot car trailer with my 2011 ram 1500 6.4 hemi all the time, the 20" load range E tires made a huge difference in the tail wagging department, I don't even think about that any more. That is the only change I have done, I wish I could find some hard rubber bushings for the rear control arms but only found them in an expensive adjustable complete assembly but now with the 20" wheels tires I don't think that is a huge deal now.

The funny thing is the factory tow rating went down with 20" tires.

yeah the factory says and does a lot of weird stuff but it tows way better now.

I tow my 20 ft Haulmark with My Dart and sometimes my 92 D150 all over the place with my 08 H.Q.C. 1500 4x4 . 3.91 gear , I installed a cold air intake and cat back exhaust and it really woke it up, I was tempted to install an aftermarket programmer but the H.P. gains were't enough to justify the cost. Also I tow in O/D off mode less shifting and more power than in trailer tow mode.