Cash flow is a little tight, but appreciation has been healthy and sustainable.

I'm looking to clean up my LLC containing a duplex, make a solid plan going forth, & file taxes in most advantageously way possible. 

People don't make as many babies as they used to, so those folks view the extra rooms as just extra stuff to clean, they aren't going to AirBnB the home to potential child molesters where their 3 year old and 1 year old live.

You just need to make sure to screen them properly and make sure they are clean, quiet, and respectful.

perfectly healthy trees falling ect it is usually considered an act of god or something along those lines and they should go to their car insurance.  

Grease dirt and smears will be washed clean.

Would this be considered clean title, or if not, what would I have to do to clean up the title? 

You just have to do it at the lock, so maybe you can get your cleaning crew to delete the old one and add the new one.

You could lose that month's rent, utilities, and be faced with $500 - $1,000 in cleaning and repairs.

I would tell him as long as he leaves the property clean so it can be rented .you will not persue him in court and you will still give him a reference.