Hello guys I am new here so forgive me if this isn't allowed or it's the incorrect format but I have uploaded a video to YouTube explaining what I am dealing with:
If you are unable to watch the video, there is dark fluid (looks like engine oil) leaking out of the transmission bellhousing inspection/weeping hole - sounds like rear main seal leak, right? However, there's also a leak at the rear of the transmission (fluid is lighter than the bellhousing leak) but looks like its coming from a point higher on the transmission than the bellhousing inspection/weep hole. So, maybe it's the oil pan gasket and the fluid is just dripping down. But how would it be leaking from inside the bellhousing then? Maybe it's a RMS leak & a transmission leak.

I would try to fix it myself using process of elimination but I don't have the time at the moment and if it is the rear main seal then I would like to take it to a place that specializes in F-trucks - considering it apparently had the RMS replaced a year ago (the mechanics at the shop told me "sometimes general mechanics don't know how to properly replace the RMS' on these trucks and install them incorrectly".

Here is the description that I added to the YouTube video:
This is an 1988 Ford F-150 with a 5.0L 302 connected to an M5ODR2 transmission. The truck has 188,000kms on it and has supposedly had the rear main seal replaced a year ago and a power steering fluid leak fixed 6 months ago.

I'm new to Ford trucks and haven't had the time to give it a really thorough degreasing or to experiment with potential solutions.

I took it to a mechanic for an overlook and they said it could maybe be the rear main seal as a lot of the fluid is at the rear of the motor and the valve heads (although dirty) didn’t look soaking wet. They also said that the fluid at the rear of the transmission could be from the same source. However, if it is the rear main seal leaking then I don’t understand how there would be fluid kind of high up on the rear of the transmission. That same shop said I wouldn’t be able to bring the truck in for atleast a month (they are the only local F-series specialists). If it is the rear main seal I won’t drive it because I don’t want to ruin the clutch.

Research online says that oil leaking out of the bellhousing could either be RMS or valley cover gasket. If it was the valley cover gasket, would that explain the fluid making its way to the rear of the transmission?

Does this look like multiple leaks? 1 big leak higher up that is finding its way down to look like a RMS leak?

Any advice or observations would help immensely.

 

That does not look like a rear main leak to me
Maybe they got that part fixed
Dye is your friend
Steam clean it all off and add dye to the engine oil. Retest with the UV light after a road test

 

manicmechanic007, i'd like to say you are correct. The previous owners said that they had the rear main seal replaced less than 12 months ago, and that they are confident that it shouldn't be leaking again. I took the inspeciton rubber off the transmission today and there was a lot of dirty black oil inside the bellhousing. Which made me even more hesitant to drive it because I don't want the clutch to slip (due to the oil). Then I had a thought - maybe the previous owners did have the rear main seal replaced but the mechanic didn't clean inside the bellhousing and the oil I am seeing is the old oil prior to the replacement. If that is the case, then I am assuming oil pan gasket or valve cover gasket.

 

I will add that I have been planning on doing a dye test, I think that given my circumstances - a dye test is the best bang for my buck. Thank you for reminding me.

 

If you get to it quick enough, you can sometimes pinpoint the leak with the dye
If you wait too long on the road test the dye will be all over (from hell to breakfast)
Those pan gaskets used to start coming out (the brown silicone ones)
A good visual inspection of the pan gasket all the way around is what I would do next