Issues towing 36 or 37 foot TT?

I think you'd be fine with a HD diesel, but I also think fifth wheels make a lot more sense when you get into those lengths. Not only do they tow better, they make for a shorter package going down the road. Just my two cents.

We tow a 33' TT with wd hitch and it has sway retardants built in the hitch. We tow with a 1 ton dully and at times I have to check to see if it is still there.

When my van broke a motor mount in October, the towing company sent their crew cab F350 SRW flatbed for my trailer. He did not enjoy the tow (I even hooked up the WD bars after he almost wrecked without them) and generally could not go over 45 and keep it straight.

OTOH - it tows fine behind my van but I can certainly tell its back there.

Have pulled a 36 5er and a 35 ft TT.Proper set up is the thing.Yea they pull and trail much different.If you do trailers then you will have no problem

Can it be done? Yes, depending on hitch and tongue weights it can be done. But honestly towing that much is going to be a strain compared to a similar sized fifth wheel.