I Give Up

[arathol]

So am I using the wrong size file - I should be using 3/16th?

That is how it appears. Look up the specs for that particular chain and there should be a file size specified. There really is no one size fits all for files. File size is dictated by cutter design and you need the right size to make it work right.
The pictures don't show enough detail but it seems that there is not a good edge on the top of the cutter. The angle looks far to steep.

 

[memory]

If your chain is .325 pitch, then you should be using a 3/16 file.

Don't worry, you will get the hang of it. It just takes time and practice. Until recently I had no idea what I was doing. I am still no pro by a long shot but I am getting better.