@Theresa Harris My neighbour has seen him drunk out in the yard a few times, but I've never witnessed that behaviour. It seems to me more like he's trying to get me to pay attention to him. He was waiting for me to get home from the office yesterday and when I pulled into the driveway he checked I was still in the car and then made a big show of being stung. He ran down the stairs and across the lawn yelling "Ow!" and waving his arm arounds. I said that if he had just been stung for the 7th time in two days that I wanted to take him to the hospital to have them looked at. He declined, unsurprisingly. The exterminator is coming to spray for the wasps today at 2 o'clock so hopefully he will calm down after this.
I asked the bylaw officer to come and inspect the door which she did this morning and said that it is functioning properly. I've been keeping a very detailed record of all of our interactions. When I get a copy of the bylaw report I feel confident that I have enough to evict him on an N7, but the current LTB resolution timeline is up to 8 months (apparently they're still behind from the pandemic backlog). I'm worried that if I served him, he would stop paying his rent and it would be financially difficult to float him for that long. I'm going to take @Bill B.'s advice above and hire a PM to avoid interaction with him in the future. If he is still harrassing me in this manner than I'll evict him regardless of the timeline. I believe that they prioritize cases of this nature above non-payment, so hopefully it won't take as long.
I think you're right and I will be there while they are installing the door. I would have been around (I work from home) but now I'm going to make sure that if he is home, I'm right there to ensure he's not bothering them.