Due to the transmission fill plug being at the top of the engine underneath a bracket making the plug nearly impossible to remove, could I use this plug that’s located on the side of the transmission just behind the front left wheel?

Those are some points for monitoring various pressures. You wont have much success in filling through there.
Those plugs go directly to valve block and clutches and it's not recommended to insert something through there.
If you can't remove the filling bolt due to the bracket, at least fill it through the fluid level plug (inner plug), with the drain plug (outer plug) in place.
Fill until it flows out, start the engine and fill again until it flows out again. This way you will have the fluid level checked in the same time.

I take the air filter box off to gain better access to the torx filler plug. You may find using a couple or three long extensions help to raise the ratchet out of the engine bay.

alex_pescaru wrote:

Those are some points for monitoring various pressures. You wont have much success in filling through there.
Those plugs go directly to valve block and clutches and it's not recommended to insert something through there.
If you can't remove the filling bolt due to the bracket, at least fill it through the fluid level plug (inner plug), with the drain plug (outer plug) in place.
Fill until it flows out, start the engine and fill again until it flows out again. This way you will have the fluid level checked in the same time.

I put a photo in my gallery of this plug.

Lando-Rover Calrissian wrote:

would it hurt anything if I do put fluid in there? What type of tool would I use to fill from the level plug?

I’m just confused now, the oil filter is on the opposite side of the engine compartment.

I was talking about transmission oil cooler, not oil filter.
We are talking here about the automatic transmission, right?

I had the same problem on my Evoque due to the electric gearchange mechanism restricting access to the filler plug. Here’s how I did mine:

https://www.evoqueownersclub.co.uk/forum/2...tures.html Past: FL2 TD4 HSE Auto
Evoque SD4 Dynamic Lux Auto
Present: Audi A3 S Line.

alex_pescaru wrote:

I was talking about transmission oil cooler, not oil filter.
We are talking here about the automatic transmission, right?

Steve D wrote:

I had the same problem on my Evoque due to the electric gearchange mechanism restricting access to the filler plug. Here’s how I did mine:

https://www.evoqueownersclub.co.uk/forum/2...tures.html

So none of these options worked and I dumped even more fluid onto my driveway. Even running it up to temp and checking the level still had some run out. I know it’s low because of the amount that dropped out before. So now I’m left with one option, figure out how to pump everything out and do a factory refill. Anyone know how I can truly dump all of the fluid?

Plenty of info in this thread, you only have to look.

http://www.freel2.com/forum/topic28619.htm...ansmission (Now Sold). 2008 Freelander 2 (Nazca Sand) SE TD4 Auto. Statutory write off & on WOVR for hail damage but still road legal.
171037Km as of 09/05/22
Superchips Bluefin Flash
Nanocom Evo II (also sold)

This method assumes I know how much fluid has drained out, which I don’t know. How can I get everything out and refill the entire transmission at once?

Lando-Rover Calrissian wrote:

I put a photo in my gallery of this plug.