Q: What's the best tool to measure the rakers with?
A: Depth gauges made for saw chain, various models available from many manufacturers, but all do the same work.
Q:And is a flat file the best tool to use on them or what?
A: Yep one made specifically for saw chain, all box stores, hardwares and chainsaw dealers sell them.
Q: I once had a chain that wouldn't cut right after being sharpend, it was a chipper chain made by sabre, and I got crazy on the depth gauges and it wouldn't cut staright, it would bog down and cut unevenly, yet it threw bigger chips than my chisel stuff.
A: If you file the left side different from the right, meaning more strokes or less strokes or rakers at uneven heights, you will experience crooked cutting or pulling to one side.
Learning to file properly comes with practice, practice and more practice. Its like sex, the more practice, the more experience, the better you get or she what ever the case may be.