Tenant does not report issues timely

[Kar Sun]

I have a good tenant with a demanding schedule.

He pays on time and keeps place relatively clean.

I respond to all requests immediately and always work with him.

However, he does not follow certain parts in our contract and perhaps he has not even read it.

He tends to sit on issues because he "does not want to complain often" and "wants to be a good tenant" but then the issues accumulate and he wants the fix immediately. (fyi: there are not a lot of issues at all as the unit is well kept)

For example, we have one older AC unit that services one of the floors that has an issue with its compressor.

He knew several weeks ago that the unit was not cooling but did not report because it "was cool outside" and he was ok "not to bug us".

But now it got hotter and he wants the unit fixed right away because he cannot stand the heat.

The lower and upper floors are cool but to him it is an emergency.

Unfortunately, we have to work the kinks with the contractor and I cannot fix this in a week.

Because of his delay in reporting I cannot even get multiple bids.

I had many times straight out told him to report issues right away but it is not happening and it is causing extra stress and high costs on my end.

Tenant thinks that he is reasonable.

I have multiple safety checks in a contract that require to be followed, such as tenant needs to let me know when away from property for over 7 days so that I can come and check that everything works fine. 

Unfortunately he does not follow it.

What would you do?

Thanks.

[JD Martin]

I would not worry about jumping through hoops if he's not going to let you know about issues that aren't emergencies for you and move on with life. It's different if he's letting a pipe leak and destroy your floors or cabinets, and of course you don't want to run your compressor without freon (most units have auto shut-offs that won't let the compressor run with low freon), but things that aren't emergencies for the unit, if he doesn't tell you for weeks, then you get to them when your people are able to schedule, and that's that.