My mayor fear was going to court,  and I was able to confront both tenants.

Since there was a tenant currently living there, I would assume that some maintenance work had been done, but were there any major surprises that you were confronted with (repairs, auction process, etc.). 

I'm sure you can do an addendum to your lease adding the pet fee that both you and her sign.What was her response when you confronted her?  

It's part of my fault I am passive-aggressive and also would like to avoid a confrontation if possible.

It is always "making things happen" until it isn't.I also have had clients who are "non confrontational" say "Please ask him to stop calling me and just stopping over, he drives by 4 times a day.

Talk to her about it without being a pest or confrontational.

It would be awesome if you set a time to go see it, and confront him.

It doesn't have to be a conflict or confrontational, but you're going to have to ask why the rent was late and how he plans to make sure next month the rent is not similarly late.

Has anyone else been confronted with this or a similar problem?

When I confronted him on the jetting of the sewer, he got defensive even though it was discussed and I believe included in the quote.