Good Morning and welcome. I am Dr. Loretta, a licensed veterinarian and I am happy to answer your question.
It is not unusual for rescue cats to have this odd behavior because they are afraid of just about everything. Since he has chnaged homes a number of times, Monty is confused and afraid. This will take time and patience to help Monty past this.
First take Monty to your vet for an exam. There are medical conditions that can cause such odd behavior and treatment could resolve this. If this is ruled out, then other steps can be taken.
Next, purchase Feliway at the pet store.This is a feline pheromone that acts as a calming agent and will decrease anxiety. Follow the directions on the bottle and use the diffuser in areas that Monty frequents. Then purchase long lasting toys such as a feline kong that will distract him from his fears, The more he tolerates the things he fears, the more used to them he will get...this is Desensitization.
If he is having a hard time, your vet will have medication to help prince through this such as Clomicalm.
This LINK has other enrichment ideas to distract Monty.
Does that make sense to you?
Please let me know if you have ANY other questions. My goal is to give you 100% satisfaction and if you are not yet satisfied, please Reply so I can clarify for you
Sincerely, Dr. Loretta