I really think he was into massage with a "happy ending". I think, for legal reasons, he couldn't solicit it and made the suggestion in private, in person. Without evidence, I also think there was additional compensation transacted. I personally don't believe there was anything but consensual "interaction" and don't hold a grudge for his dealings. I can only say that this is how things add up for me and I may very well be wrong, but I can understand a "lack of remorse" if correct.
I think what you described is (mostly) within the range of potential outcomes - in at least some of the cases and quite possibly most of them. The guy (allegedly) had massages with 66 different women over a 17 month period, 25 filed suit, 20 settled, the NFL presented 4, and I've never thought it was a gaffe on Rusty Hardin's part to say (paraphrasing) happy endings aren't illegal. That math is...an eyebrow raiser.
If you haven't read the report you should though. What Robinson wrote about those 4 cases painted a consistent picture and I think it's fair to assume those plaintiffs did not have consensual experiences. The others? Well...we'll probably never know, but based on what we do know I don't think your theory is crazy.
I read Sue Robison's report. It looks like Watson's team offered very little in the way of defense, essentially
So your theory is that Watson had sex with a bunch of prostitutes and then those prostitutes all got together and decided to sue him for unwanted sexual advances with no worries about being outed as prostitutes.
Sounds plausible.
My theory is that he wanted a massage ending with release. He alluded to it in texts prior to the actual encounter, but would not be specific. Some of the MTs were amenable (42 of 66?), some were not, and some were genuinely surprised at the suggestion. In his eyes, he was doing nothing wrong inasmuch as he was only seeking, not demanding, the encounter. Do I think the women were prostitutes? No. Nor do I believe he thought of them that way. He thought of them as women he might "Hook up" with for a one-night stand. (Though, I readily admit I've never spoken to him or do I know him at all.)
Regarding the allegations, I found the majority to be identical, boilerplate filings. Several, I found to be implausible, and I wonder if this isn't the reason the NFL didn't present them all.
All-in-all, that's how it adds up to me.