Kitty stress..

I don't even know where to start?
I have 2 male cats, bee is a 1.5 years old mr.oliver is around 4 years. Both neutered.
I got bee first, I found him outside and he was around 4 months old. I've had him ever since. Mr.Oliver I took inside for the winter since he was 3 years old and very feral. but decided to keep him. I did the introducing process which took about 2 weeks.

mr. Oliver is a very quiet, sweet boy. Bee is a menace. He's crazy. He does circles of the apartment. And if I'm sitting on the couch he does circles around me, where he starts on the floor jumps to the arm rest, then head rest, second arm rest,back to the floor. He attacks me when I sleep. And I should post a video I have of him doing flips in the air on my bed. I also come home from work to huge messes about 1-2x a week. 2 days ago, well at work, he jumped on the counter, to the top of the fridge, opened the top cupboard where I keep mr.oliver's food, chewed the bag open and kibble was all over the apartment. Not to mention he's allergic to mr.olivers vet food, so he also got sick everywhere. Last week, he got into my closet pulled down all the clothes hanging and chewed up a shoe box. He can open closed doors that have knobs. Those are just a few things to give you an idea of crazy this cat is. His next favourite thing to do is attack mr.oliver. Mr. Oliver doesn't fight back he just sits in a ball and cries. He use to fight back but it's like he's given up? the attacking is getting bad now though. It started getting bad a few months ago. And mr.olive keeps getting utis. And my vet and I have narrowed it down to stress related. So it's actually affecting his health now. Mr.oliver can't move anywhere without bee attacking. And I've noticed bee controls where he's aloud to go and lay or play in the apartment. He's also started moving around really close to the ground again like he did back when I first brought him inside. But when I seperate them, even at night, at 2am when the halls in my apartment building are quiet, I bring bee to the hall and play fetch or with the lazer pointer. Mr.oliver sits at the door and cries the whole time but doesn't want to come out? If I try and do a re-introductory they both lay by the door crying and scratching? And both sneaking out? I have had them seperated for almost 3 hours right now, and bee has sat there crying the whole time, scratching at the door and jumping at the knob. He does not give up and go find something else to do, he actually cries for hours. mr. Oliver hates being stuck in the room, and he's also crying. But the stress and attacks are getting too bad I can't afford all these Utis. I've thought about giving one up, but bee is too crazy I'm affraid someone else would take him for a drive to the country and dump him. And that thought breaks my heart. And Mr.oliver is a feral and always will be. You can't pick him up or pet him, and it took him 6 months to come out from under my bed well I wasn't sleeping. So he's a cat I enjoy for other reasons other then his affection. And I don't think anyone that would adopt him would appreciate him. And he has health issues.

So not sure what to do? Mr. Oliver is stressed actually sick, I'm stressed running around yelling squirting a spray bottle nonstop. And I think bee is boss and controls the place, including me! Anyways, I use to love cats and now I'm sure these will be my first and last, if I knew I would be sitting in my car after work, debating whether or not to go home and deal with the stress or drive around for a bit and avoid the whole situation, not sure I would have ever brought a cat in from outside.

I guess I should mention. I've tried feliway, calming treats, melatonin, calming colar is on, and even meds from the vet, ware off bee within an hour or two. He gets 30min of hardcore play before work, 45 min before bed. I have cat tunnels, cat shelves, window beds, toys, 2 cat trees. He is not bored. I have no idea why they went from civil and just play fighting to full blown attacks and craziness. I wish cats could go to therapists/psychologist lol, or a behaviouralist! I've grown up in a household with +4 cats and 2+ dogs my whole life, as my mamabear is an animal lover, and even she has no idea what I should do?

I'm sorry, I won't be much help but I have been in a situation where my cats did not get along very well at all and it's tough!

I don't know what your financial situation is like but as a last resort you could try an animal or pet behaviourist. They don't come cheap but might have some idea's. It sounds to me as though you've tried pretty much everything.

Just curious, what happens when you separate them into their own rooms but use a wedge to keep the door open just a centimetre or two so they can see and touch each other but can't actually get at each other?

It sounds like the introductory process was rushed. It can take months to have your cats properly adjust to each other, and you have to go at their pace.

I suggest starting over. One gets a room and the other gets to roam the apartment. You switch them out sometimes, and switch the rooms around so they both get to be confident in all areas of the house. Watch Jackson Galaxy videos on cat introduction. You feed them on either side of a door, and then a gate where they can see each other, moving the bowls closer at their pace.