Ideal gap? well ideally as much as you can get? How small a gap can you go? Well you need something for the gasket to seal on, i can't give you a set figure, but there is "enough meat" and then there is "that's not enough meat"
To measure a piston, you measure the skirt adjacent to the gudgeon pin. Piston manufacturers might specify a certain height to measure at, but it is normally the height of the pin. As far as i know. (could be wrong)
The ideal place to measure the bore is all over the place. You can get special micrometers for measuring cylinder bores i think, but i just use a t-bar and measure that with a normal micrometer. It is easy to use the t-bar to measure from top to bottom and different sides.
However the place most likely to wear would be where the top ring comes up to the top of the bore.
If i'm looking at a block that i don't want to rebore, i will just run a hone similar to this
http://www.google.com/imgres?um=1&sa=N& ... =39&ty=113 down it, and i can quickly see how much of a lip and any hollow spots etc. Then i can decide whether it will hone out or need a rebore. If it does hone out then i will measure it and see if it's still any good.