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elcornholioMounting bindings multiple times can be hard on the ski (it will increase the likelihood that the ski will snap) but as long as you use epoxy or wood glue to fill the holes, you should be fine.
perryhunterDon't very familiar with this. But I guess there's no big issues.
freeski1620In the shop 3 sets of holes is usually my max. Think about how easy perforated paper rips versus a whole sheet. The more holes in the ski the weaker it becomes but I can never recall seeing a ski snapped because of the amount of holes in it.
Generally if remounting with the same binding I will re use one of the old sets of holes. Toe or heel and only put in one new set.
In regards to filling holes it's very important to do so using plug and wood glue to keep the core dry. One easy way to snap a ski is to let water in and rot the core. Then it is very likely to snap because of the rotten core.
Hope that helps!