They are normal to think about, but these kind of questions are going to give you limited beliefs and prevent you from moving forward on a potentially great property.

I'm in a unique situation where my DTI ratio is preventing me from buying a house at even half the monthly payment I've been paying in rent for years (I actually pay early every month).

The big wholesaling shops in our states are spending their own resources to actively lobby for wholesaling to prevent it from being banned.   

But I do keep boundaries to prevent micro managing.

I am just trying to prevent you from going down the same path that many of us did.  

If your lease doesn't explicitly address pest control responsibilities, it’s worth reviewing and considering adding a pest clause in the future to prevent disputes by adding every single pest.

Let's say someone was bungee jumping off a balcony railing and the railing broke and they fell, injuring themselves.They could sue the property (ownership LLC) because the railing was "not secure".They could sue the manager (management LLC) for not ensuring the railing was secure.They probably will sue both and let the court sort it out.I don't see how 1% ownership of one LLC to another prevents any of the above from happening.

The better question is to figure out how to get insurance and resolving the reason that is preventing it.

IMHO; UD actions are preventable actions caused by tenants failure to vacate the premises. 

Do you have something in your lease preventing tenants from AirBnBing to others on Game Day, Graduation weekend, etc?