WoW man you have a tall order here!

Personally, if I were planning on towing, I'd rather tow with something that has a lot of power. I used to haul horses with a Chevy pickup with a 305 V-8 and dreaded not having a 454 V-8 instead! A 5 cylinder OM 617 turbo diesel might be adiquate for your run of the mill two wheel trailer hauling leaves to the dump, or maybe a 14' aluminum boat, but after that?????

To answer your tranny integrity, the answer is "both" as you have already have clued yourself in! Disc slippage will generate heat and it wont matter if you have extra cooling, your still going to do damage! Again, cars in general really arent designed with towing in mind, and while you can tow, you will wear out your tranny sooner! My 84 300D had a four speed auto. There were 4 spd manual trannys available, but are rare!

There are two basic adjustments made to the auto tranny via bowden cable and modulator valve. These could be improperly adjusted and cause a good transmission to act like it is faulty. Shifting should be crisp, even bang a little bit is OK, but flaring no! (mod valve adjust) Shift points should occur for all speeds at or before 2000 rpm, depends on how far you have your foot into it!

Anti-lock became standard after 1986 I believe, but was optional before that. The anti-lock system is usually in front of either front wheel well under the hood connecting hydraulic lines from the master brake cyl.

My 84 300D did very well in the snow but not as well as my 87 300D that hosts a far more powerful 6 cylinder turbo diesel and actually does get 30 mpg at 80 mph, but don't expect that from the 617 5 cylinder, 23 - 25 on a good day!

Flames blasting out the rear? you mean like nitro? I don't think so, you need to get better aquainted with knowledge of diesels! They generally run much cooler than gassers, but there is a possibility of "run away" meaning they start sucking crank case oil uncontrolably and climb rpms to red line and blow-up, a very rare thing, but does happen once in a blue moon. That's why they call it "run away" because in most cases that is your only option!

Gotta run................BB