What that means is, every infiltration attempt will fail. Because the DM will simply keep throwing checks until one fails, and then the whole thing falls apart because every fail is a catastrophic failure. There are no degrees of failure. Did you fail your deception check? Yes, then the other person automatically sees through your disguise and raises the alarm.
Every.... single... time.
Yep. I have seen this too, not from every DM but from some of them. Sometimes it is a desire to force failure without appearing to force it. Most of the time, however, I think it's just a lack of skill, and being bad at translating "challenging but achievable" into iterated probability.
It's one of the (many) reasons why I think rules should be designed, not for bad DMs, not even for good DMs, but for
mediocre DMs and
subpar but well-meaning DMs.
Because bad rules can hardly hold back a great DM, and good rules can't fix a crappy DM. But good rules can really help a mediocre DM a lot, and can help a subpar but well-meaning DM learn to become a better one.
Then you'll just have to accept the drawbacks with the benefits.
See, this is a thing that's been allowed to ruin D&D's design ever since WotC took over (and arguably, even well before then): players complaining about drawbacks and yet still wanting the associated benefits, and the designers acting on those complaints.
Not at all.
Having a deity constantly watching your every move and pulling the plug the instant you slip up is not, in any way, an inherent or required element here. You can--and should--design for a wider berth. Investiture isn't a requirement, and you were extremely skeptical of it when you thought it was. Why are
your preferred limitations somehow the necessary, critical element keeping the game high-quality, where their removal has ruined the game, but
others' preferred limitations an unacceptable impediment preventing interesting stories or limiting the DM from portraying the kind of world they want to portray?
Simply put, you haven't even tried to respond to the charge of double standards here. What makes
your drawbacks a wonderful and essential building block of the game, foolishly cast aside by designers at the request of immature and ignorant players, but a different slate of drawbacks would be an unacceptable intrusion into DM authority and player freedom? It would seem to me you can't have it both ways.