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How many miles do you put on the overdrive unit before it fails?
Are you towing that trailer in overdrive?
What is failing in the overdrive unit?
There is a switching valve in the valvebody that can restricted cooler flow and cause problems,sonnax makes update one to give you 40% more cooler flow which is a must while towing in my opinion.
How does the pan look when you changed the filter?

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The trans was built about a year ago, I had 165K trouble-free miles on the trans before I blew the engine. The trans was starting to slip a little so while I was getting another engine to put in I had the trans rebuilt. The overdrive first went out about two months after I started driving it again, it was the large snap ring that broke. They took the trans out and replaced the snap ring and put it back in. The next time it was a solenoid, they did the same thing. Then one cooler line started leaking, fixed that then the two front lines rubbed together and started leaking. After that the overdrive started going in when it felt like it, nothing I did would make it kick in or out. Then it got to the point that it would only kick in when it was good and warm, and then not all the time. If finally quit working altogether but I had to continue to use the truck as I had sold my other truck and it was all I had. When it started leaking again is when I took it to another trans mechanic and he found it leaking on the top of the case somewhere, that is all I know because I had to borrow a truck to do my latest haul and just got back. I have not changed the filter lately as I have less than 20K miles on it since it was rebuilt.