I've always heard the 75w-140 was the best choice but I'm willing to take your word that 85w-90 is just fine.

 

Just fill it up on the kick stand and call it a winner. This is not surgery...
Ditto on the 85w-90 (Valvoline) for me...

 

Do I need Dextron III for the primary ?

 

i've used 20w50 harley motor oil, 85w90 and 75w140 in my trans, it's all the same as far as i'm concerned. i go to my local farm store and get their farm tractor gear oil and use that because nothing takes more abuse than a farm tractor gear box.

 

While I disagree with filling it on the kickstand it looks like I sit corrected (I am sitting on my *** while I type this after all) on the tranny fluid.

I will probably try filling it on the kickstand and then straightening the bike up to see where the level is with the bike upright just out of curiosity.

 

I am surprised nobody mentioned Redline Shockproof.

 

Now that you mentioned it I use Redline Shockproof. Seems to work fine. Who knows if it is better than any other synthetic gear lube.....

 

I think I got lucky. I had indeed overfilled the primary but about 1/2 a pint. Took it on a test run and it shifted fine. Fingers crossed!

 

Here is the correct primary lube level for all big twins since late `84, it should not be higher than this, but a little lower won`t hurt a thing (bike vertical):

 

FIXED ! Found the primary chain adjuster loose and dropped down about 4 clicks. Re-adjusted and it shifts flawlessly. I can actually find neutral again. Actually fixed 2 issues. I also had a surge that I thought was due to a lean carburetor but turns out it was the loose primary chain. Thanks for all of the suggestions!