Hey there!

I have a 1988 2wd pickup with a 22r.

A friend of mine is selling me a 1987 2wd 22r. (Gonna be my next project.) Only problem is - I have to go get it.

The plan is to drive from New Orleans to Arkansas (somewhere west of Memphis area) and tow it back with my truck, reverse on a uhaul dolly.

So, a Toyota pickup pulling a Toyota pickup. What do you think? I’ll obviously take it slow, and I know braking will be my biggest issue.

Think I’ll make it?

 

It can be done. I towed a 1967 Mustang on a dolly 4 hours with my 88 Pickup 4x4. Your 2WD is lower which might be more stable, but it's also lighter which goes against stability. The old Mustang weighs about 3300 pounds according to Google, but mine was fairly stripped so maybe only 3000 pounds as I had it. Seems comparable to your proposed towed vehicle. My drive was also fairly flat. Hills would be slow going up and potentially scary going down.

You mentioned using a u-haul dolly. Those all have surge brakes which is good. My dolly isn't as nice and has no brakes. You generally want to do your braking in a straight line. When you brake, the back end of the truck gets very light. If you brake in a turn with a trailer behind you, the trailer will push the back of the truck sideway and you'll jack-knife.

Make sure your hitch receiver is in good shape and safely attached to your truck. Take your time. Check the load often.

 

I see caravans of Toyota trucks towing other Toyota trucks, heading east on I-10 every day.

 

I recommend this video to help you assess your towing decision:
It does an excellent job of illustrating what creates stability, and what creates a hazard. Great demonstrations.