Alright guys. I've been doing this since I was 7 years old [which makes it 18 years], and have built 326 engines, with documentation on each, so how about we quit with the pissing contests?

As for gapping your rings. Yes, you ABSOLUTELY should gap your rings EVERY TIME YOU CHANGE THEM.

Part of gapping your rings is inserting them into the bore for measurement! Obviously, if they're within spec for the cylinder you're going to use it in, you're done! If they're too tight, then you file them, grind them, whatever method of opening up the gap you feel comfortable in.

If you're really anal about performance, you go with aftermarket rings the correct size, which are pretty much guaranteed to be too tight and trim for the lower end of the tolerance range.

As for the orientation of your ring gaps, just make sure no two gaps are lined up. The reason there are 2 'C' marks is because the manual you're using is showing you there are two places you have to chose where to put the gap.