After a few test fit installs and checking out a couple of different shifters for fit too, I decided I was bloody NOT installing any more shifters after the transmission was in the car. I can, and I have, but really really don't want to anymore. I'll stick with my filling from underneath. Could be just me though.
I actually have one of the weird transmission-driven power steering pumps from a Honda. I have a pair of hoses on it. Chuck it in a drill and put the hoses where you need them. Pull the trigger and transfer whatever fluid you like, easy peasy. I actually concocted one of these at work and liked it so much I made another to use at home. The reason I made it is because I got sick of buying hand-held fluid transfer pumps that work a few times then quit. Especially if you don't use it for a year or so in between times. The Honda pumps have yet to fail me. They work in reverse too. You need to evacuate brake fluid from vacuum booster because the master cylinder rear seal failed? Got a nine inch rear end combination that has fill plug but no drain plug? Here, hold my beer.
If anyone is actually interested I'll take a picture of one of the pumps. They're off like 1993 Civics or something. But really, cap on a bottle with a hose, and I can fill a T5 in just few minutes just squeezing the bottle. Not enough trouble to merit dragging out a pump. And If I've been working on a T5, the car's up in the air already, right?
Last thought, every method of filling in this thread is fine. Just use whichever one fits your particular circumstances.