You know that he withheld the info to ask for a date, right? If he was so concerned he could've just told her after their shift was over outside of the hotel premise. Standing up for Lena against Axel was commendable and I don't deny that, but expecting a reward for the deed is shifty. He thinks just because he stood up for her makes him eligible for Lena's pants. He helped for his selfish needs not for her sake.
Spilling the beer by Perry on him on a bad day is understandable but Perry did apologise to him. In chapter 11, Robert does the same to Sen and is ready to fight him without apologising; meanwhile, he is the one who spilt the beer on Sen. He mocks Perry's stutter at the museum, even if you didn't fight him outside the bar.
Hooking up with Robert/Mike will give you bad Jess. Both are equally bad. One is a grade-A asshole the other is a cheating cunt.
Stan never sniffed their panties. It was Lola who dropped it on his bedroom floor. It's debunked later when Lena/Louise catch Lola doing the zoomies. Lola is like a guardian and a moral compass for Lena. Animals can easily discern between genuine or trash people. If Ian cheats he is also hissed at by Lola.
Axel/Robert/Mike/Seymour are all manipulators on a different level.
Wade is trying to get his life back up. While playing video games and aiming for the pro-scene he is also actively searching for other jobs. He's just caught in a wrong moment where Cindy is feeling adventurous and he is not able to reciprocate it. Perry is trash but he's been given some guiding hands by Ian and he is open for a change.
You need to understand that in order for Robert to share this confidential information with Lena he is risking work place incident / his job. He could get in trouble with his boss for sharing this information with Lena.
Making sure ahead of time that she likes him before telling her this information is not evil, it just makes good sense on his part to wait and see if she likes him before taking this risk for her because there are risks involved for him in being a blabber mouth. Telling her could lead to him losing his job, or not getting a promotion. It could effect him negatively.
He tries to help her out keeping her job longer and all that when they are hooking up because that just makes sense. It's the same deal with Minerva and Ian.
Plus, it is a job waiting tables. She has 2 other jobs. The online / model stuff, and the coffee shop. So losing one of her 3 jobs would not be catastrophic for Lena. I don't think she would wind up homeless. She has 2 room mates sharing in the bills.
It's not like she is the soul bread winner of a family, and it's the only income she has, and she has a few little kids to feed. She will land on her feet. People get let go from jobs every day. That is a part of life.
If you are going to put your neck out there for someone it would make the most sense to make sure they will appreciate it and not just use you.
I got a short personal story for you where I helped someone out and it bit me in the ass. I was like 17. I was walking to work at a fastfood joint. There was a woman whose car broke down, and she didn't know how to change a tire. She was like 25. She was kinda cute. So, I walked over and asked "Do you need any help?" She was thankful for my help, but not that thankful. After I was done changing her tire I asked her, "Could I get a ride to work?" She was like "No, I am in a hurry and I don't give rides to strangers." It was like 3 minutes by car or 15 minutes by foot up the road. It made me late for work and then I lost my job for being late.
Robert may have had similar incident where helping someone bit him on the ass. So, maybe that is why he did what he did.