1. Well if you watched the movie you would see that everyone who was wearing a suit was some kind of informant. If they all came in and talked to one another in their regular forms their informant identities would be reveled and all would be lost. Both of the main people wearing the suits ends up being two people who were banging one another so that would mess things up if they both knew who one another were.
2. I noticed that Bob was pretty much a brain dead zombie by the time he got to the farm. Which is why I think the company decided to send him there. His mind turned into mush which would be perfect to use as people to care for their hidden illegal drug growing business. If he was of sound mind and just addicted they wouldn't be able to trust him. That guy with the suit even talked to him as if he could convince him that he didn't see what he thought he saw but only hallucinated it . I think that Donna put him there thinking that he would be able to realize what's going on and report back, which is what I also think happened when he grabbed the flower and said he's going to take it back to his "friends". Friends are probably going to end up being Donna and her partners.
I think this whole movie and Donna's whole character as Bobs girlfriend and as his boss was a way for Donna to break Bob down enough to get him into the deepest part of New Path. She probably helped his addiction and kept him out of jail to make him the person he was. She played him the whole time he was under cover. She may not have known who we was undercover at first but once she found out she played him.
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