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I'm looking at an 88 F250 with 80,000 miles and the guy wants $1875 for it. Its the big engine and extended cab, but not 4x4. He pulled a fifth wheel with it and "can't remember ever changing the tranny fluid". He says if it sits a month it has trouble moving before its warmed up. The price looks interesting, but I'm wondering if I should avoid it nonetheless.
Pull out the dipstick and look at the fluid. It shouldn't be dark. If it is, it needs to be changed at a minimum, and it's likely that something is toast. The fluid shouldn't burn.
There is a filter in there that if it is plugged up, it will reduce pressure and result in the tranny not holding tightly, but you can't really tell that without tearing the pan off.
As part of purchasing a new to me vehicle, I'd change all the fluids - helps me get to know the beast. Is the transmission fluid/pan/filter a DIY item?