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Fix the leak but if you want to lower it every time you park it that really shouldn't be an issue. The compressor goes bad from being overworked trying to compensate for leaks and running continuously to a point it overheats. Under normal operation refilling the reservoir after a suspension command won't damage it. My rig is almost a decade old, I lower it every time I pull into the garage. No sign of the compressor giving up anytime soon. Worst case you just rebuild/replace. Personally I think using the suspension often keeps it in good working order.

As for the leak raise it up and spray soapy water on the bellows, look for bubbles. If you can't find any raise it up and listen for leaks at the hoses/valve block. Also when you experienced it deflated was it really cold out that night? That can also cause issues occasionally where valves end up freezing resulting in the car sinking.
 
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