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I would use the manual transmission for towing if there is a choice. The only concern would be if the clutch was showing signs of slipping.
If you use the Auto Tranny you need to install a good medium duty transmission cooler at the same time. I am now a firm believer that every auto tranny should have one. But that may be from the lump of coal from the wife's Mercury over the holidays. It did not have one and I put off putting one in. This March it will be getting one installed and from now on if it's title is my name and has a automatic it will get a transmission cooler.
Inga (86 245DL, Automatic, 269K)had a hitch added this last spring and she tows a 5x8 trailer. Added a VDO Transmission temp gauge as part of the "upgrade". You do have to keep switching the overdrive on and off. The manual says to leave the OD off all the time but I lived on the edge because the tach was hitting 3300 in just third. The only time I used the overdrive is when the pavement smoothed to flat and that worked quite well. 240's are not exactly towing beasts but get the job done. Made a 450 mile trip in temps in the high 90's without any issues. The transmission temp did increase about 20 degrees over the unloaded temps.
I would replace the rear springs with a set of overload springs unless you like that driving up hill feeling all the time. Also you want a good set of shocks and to check your brake pads. When you add a load to the back you want to bring your A game.
Good Luck,
Paul
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