I understand what you’re saying, but in my opinion it’s highly unlikely to be “perilous”.
The main point I wanted to make and the reason I replied to your post was that it seemed to come from a place of worry: a worry that somehow customers are constantly on the lookout for ways to not give you your money and are efficient at disseminating tips on loopholes among themselves.
I used to have worries like that a long time ago, but now it just seems silly to me to worry about such things. If there’s one thing I learned over the last few years of running my own SaaS is that most of the crap I do (good and bad) goes unnoticed by even my best customers. If they decided my product is valuable, and I don’t screw up too badly, then they just want to get on with their lives.
That’s my experience at least, but I guess it depends on the market, product, price point, etc… Have you experienced a situation where large numbers of customers use loopholes to pay less?