Having talked to lawyers about this sort of case, be prepared to speak to several to find a match, or read between the lines - when you ask questions like, “If I break this clause, what sorts of liabilities am I exposing myself to, and how often in your experience does that happen?” Be prepared for, “as my client, I don’t advise you to do that.” Not super helpful in my case, as I was trying to understand the possible outcomes and likelihoods.
The best advice I got was from a business mentor which was, “if you don’t rub it in their face, they probably won’t notice, and probably won’t care.”
Which is, as you mentioned, a probability calculation.
What I would personally guess [not legal advice] is that you rate the likelihood of your employer suing higher than they do (absent anything egregious).
