1)This depends upon how much you ride (distance on a day of riding) and snow conditions. In powder or slush, the edges will stay keenly Sharp for a long time. Ice dulls edges fast, so if you ride a lot of ice, you A) want to maintain really sharp edges and B) will need to sharpen more often. The best way to tell is to just run your finger down the edge and feel the sharpness. Try scraping the edge with your finger nail. it should whittle a thin layer of finger nail. If not, time to sharpen.
When doing just a sharpen, I do not touch the base edge at all. I use a handheld edge sharpening tool. Be sure you use the right bevel, some are 90 and some are 88 degrees. The 88 degree tool is most common for a really sharp edge for a free ride board.
2) Having both is nice, but not absolutely necessary. All you are doing with these is very slightly detuning the ragged edge from the filing. It reduces drag and makes the board less edgy. A diamond stone is also great for touching up small nicks that have a jagged edge.
3) Unless you damage the edge, you really should not need to touch the base edge at all and only sharpen the side edge maybe a handful of times in a season. If you need to file the base edge, it is pretty important to spend the money to get a good, quality file guide or just let a shop run it through the machine. The machine is going to give a much more even bevel than doing it by hand and it is a very cheap maintenance cost.
4) the "few layers of tape" to me is kind of "Mickey Mousing" it. A really good, high quality guide with what ever bevel you want (they tend to go .5, 1, 1.5, 2, 2.5 and 3 degree) will generally set you back $25 to $50 depending upon brand. Unless you throw against a brick wall they will last for life, so it`s not a bad investment if you really want to do it all.
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Edge tune up
Edge tune up
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