Ovinomancer
No flips for you!
My question was asking if you're always evaluating the situation to see if you give out free hide attempts and you respond by telling me how you do checks. The question wasn't about how you might do checks (although it's interesting you don't allow for proficiency to affect those) but if you are constantly evaluating for the opportunity to give a creature a free hide attempt.Sometimes there's no check at all because the only way someone could locate someone is to see them can not happen (the silent imp flying above the market). Other times times location will automatically be known (fighting in a swamp).
In general I don't give "free" stealth checks, I may give dex checks (no proficiency) to help set the perception DC.
Corollary to the question: how often are you giving out free hude attempts? Often, occasionally, or rarely?