When do you stop over delivering?

I decided that even though it felt like my income from renting was “fixed”, I would over deliver to my tenants by always fixing things immediately, returning the whole deposit on move out if there were no serious damages, and not raising the rent as long as they wanted to keep renewing, even if the market said it was appropriate. However, I’ve had a situation with a tenant who reported an air conditioning problem to my manager, my manager asked if he’d changed the filters which the lease said was his job, he said no. My manager said he needed to get the ac repaired himself then. The tenant then started cursing at my manager and using words that are commonly referred to as “expletives” and told him he would refuse to deal with him any longer. I honestly would have just fixed the AC, but the manager was trying to save me money, I see that. But I also don’t think it was appropriate for the tenant to say words generally considered offensive and insulting.

When I received the rent payment, the tenant had deducted $120 without explanation. I asked the manager to contact him. He received no response. The tenant was able to find my personal email address and sent me a mail directly. He said if we wanted to keep him as a tenant, we needed to deal with him directly and that it was weird we use a manger and he thought our manager was inappropriate and “infuriating” as he has been extra busy keeping his business afloat. He took it upon himself to deduct the rent, and absolutely won’t work with my manager on anything and said he’d get his own manager if we refused to communicate.

I live outside the country at this time, and also, I have a strict policy that I decided on years ago that I do not want to deal with tenants directly. This is why I chose to pay someone…so someone else can get cursed at first thing in the morning, it’s worth it to me.

I have also reduced this tenant’s rent when he’s requested during contract negotiations and never charged a late fee when he’s forgotten to pay and I’ve had to have someone reach out, I feel I’ve been more than fair with this tenant and I’m sorry if he’s having trouble due to Covid-19. The space he occupies is a live/work loft for commercial use, and he’s a fashion designer. I know that industry has taken a hit. I would have authorized payment for the AC repair if he’d asked or been civil to my employee, but he didn’t.

But I feel kind of violated with unauthorized rent deductions, the way he’s treating my manager, and also using my personal email. He’s up for a rent renewal and I feel as though I can’t afford to deal with the cost of a new tenant, but I also want to keep my boundaries and not give anymore. I don’t know how far over delivering goes when someone is unhappy. I feel like I’m the landlord I would have loved to have had when I was renting. I allow dogs too, for fucks sakes, not that he has one. Maybe he should get one. Sounds like he needs a friend.