Towing with a double cab

I need to tow a small utility trailer with about 2k in it, the trailer probably weighs about 300 so the load will be approximately 2300# when all said and done. I've never towed anything with an automatic transmission before so this is all new to me. What do I need to watch out for and dos and don'ts? Keep the overdrive off the whole time or just in hilly areas? I've heard that keeping it in O/D can ruin the transmission if done improperly.

 

Is this going to be a once and done thing ??

Then maybe your going to drag this trailer around for the next 20,000 miles or more .

If more then once and done a stand alone transmission cooler and temperature gauge would be first on my list

 

Search is your friend. It's on the top right. You'll find things like this thread - directly answering your questions and more.

The Tacoma Towing Bible

 

Probably once in a while, maybe twice a year at most.