Hi Matt,
Well a couple of things. First is backmasking. You really only need to backmask (unless your are concerned about weight) if color butt against each other. I you plan a paint scheme that has some space between trim colors, then you can generally tape all the trim colors at once then just cover up whatever you don't want painted for each color then pull all the tape at once. If the trim color back up against each other, then you can tape of the lines and overspray onto areas that are going to get another color anyway. It takes some planning to minimize the amount of taping and masking to do. Taping refers to the tape (usually vinyl) that you use for the paint edge. Masking is what you do to cover the area you don't want painted.
As far as checkerboard, there are a number of ways to do it and I'm sure others will chime in with their own methods. With me, it depends on how complicated the scheme is and how many compound curves it goes around. If it's mostly flat or relatively flat areas, then I use vinyl or frisket paper to cut out the checkerboard and lay it out. If the checkerboar wraps around wing tips or other compound curve surfaces, then I just use vinyl tape and methodically tape the thing off (often a several hour job). One method I tried on the last checkerboard scheme I did was to use paint on vinyl then cut the area on the plane. Realy tedious and in some ways harder since you have to be ridiculously careful not to puncture paper or cut into the wood. The stuff cuts very, very easily and will tear easily. Takes some practice.
Hope that helps. Some anyway. If you can find the thread on Eric Viglione's last plane, he shows a very good strategy for taping without a lot of backmasking.