Maybe a load assist bar to load from the side?

I've towed with 1/2 tons, 3/4 tons, and now have a Tacoma V6 with the tow package (6500# rated) to tow my 3700# dry wt (45-4700#) total wt trailer.

You may already know all this and didn't ask for it, but I'll put it out there,

Maybe it'll help with your truck buying choices.

Of course all IMO,

First, make sure your trailer brakes and controller are in top condition and properly adjusted,
Unless you go 3/4 ton and maybe even then get a load leveling hitch setup,
If it doesn't have a trans cooler, put one in, unless it's a rare manual trans,
Make sure the engine cooling system can handle the excess heat from towing,
Cover all the bases, tires, belts, hoses, (I say this because I used to gloss over some of this stuff)

I recently got a new trailer and weighed everything as I moved stuff from one to the other, just for the GF and I we had about 650# over the dry wt sticker, remember that sticker is "as built" and doesn't include the battery or propane tanks,

I am NOT recommending a Tacoma, but the above is what I did, since the Tacoma I got had a standard suspension (pretty soft) I added air bags and a top of the line brake controller. (already had the load leveling hitch)

Last year we went thru the southwest, starting here going thru Bakersfield, Las Vegas and thru the Utah Canyon Country, I was a little concerned but while dragging that trailer from sea level to over 8000 ft the setup performed flawlessly.

5% towing a 7k lb travel trailer, 95% other.  I understand the limitations of half tons, and am open to a 3/4 ton diesel, just waiting on the right deal to come my way.

Welcome to the Madness!  What kayak did you get?