He may be trying to avoid confrontation with you and is "raising his own rent" to the most he can afford in hopes you wont raise it to full market rent. 

I'm aware most communication which involves confrontation, isn't best suited by a ping.

To make it easier I have added the holdover cost to my lease which is about 1.5x the daily rent rounded which I feel eliminates hard feelings or confrontation at the end.  

I stink at the confrontational interactions with tenants, but I do it because it's what has to be done unless I hire a manager. 

Ask their advice up front and avoid a confrontational relationship because they can keep you awake at night.

It confronts one's pre-dispositions but because the story takes place in a different place and time, it does not provoke a defensive response.Millionaire Real Estate Investor by KellerThe One Thing by Keller and PapasanTribe of Millionaires by Osborn

I am wondering if anyone has confronted a similar situation, if I am missing something, and if there are better approaches.Thanks!

But if his work is sub-standard, then confront him about that and mention the possibility of bringing a lawyer aboard.

The whole time making a lot of noise, disturbing a neighbor and being rude to the neighbor when confronted.

Sounds like you have an agent who has an issue with "confrontations" and would rather avoid them.