I think what you do (finding faults in the system and stuff like that) cannot be called skepticism. I think it is called "having an eye for detail" and using that to make sure things work right. Skepticism (for me at least) is being dismissive of an idea, mostly without even going through all aspects of it (which is what usually happens).

Even if the what ifs are being asked in a somewhat negative context, I say, we should still ask the what ifs. Because, only after that do we begin looking for further answers.