Absolutely Kaep should have known it.
One of the lawyers/"team reps" advising him is Mark Geragos. He's a high-power celebrity attorney in the Bay who absolutely knew that some workout waiver was going to be prerequisite. He and Kaep's high-powered "team" should have demanded this waiver no later than Wednesday or the deal would be off. Even Kaep without his "Team" knew some sort of paperwork was coming, and with his skepticism should have demanded the paperwork be promptly delivered or the deal was off. Yes NFL should have presented it earlier, but since they didn't, it was on Kaep's Team to ask.
I mean, that's what we do when we buy a house.
As far as what it said, SI got ahold of it and turned it over to their writer-lawyer Mccann, who says it only addresses physical injury explicitly but could be argued to mean "more." I mean, what is "more"? Two low-level scouts sitting on the sidelines saying, "Ah, I can't believe I missed Georgia-Auburn for THIS?" The NFL was going to have 25 teams there. They couldn't control what the reps said amongst themselves, so they wanted to be indemnified.
Had he gone through with the league-sponsored workout, it's very possible that a couple of teams would have recommended a followup based on initial convo. Which would have come down to, if we bring you in, what can we expect with the off-field stuff. Not just kneeling. No one wants to be the Ravens and have his GF tweet a racist meme saying they were the racists.
No one wants to be crucified for giving him a chance, which is why he hasn't gotten one.