What I am trying to wrap my head around is the cultural differences not to mention the language barrier.

"Property listings may not include language that violates the Fair Housing Laws.

This would be state specific as an LLC, so the language needed or set up might be different depending on the state or states you operate in. 

I can understand being nervous about meeting new people  - especially in a field that you are new too - you probably have this image of a bunch of sophisticated investors sitting around discussing their latest acquisitions and and using lots of confusing language  - but in reality real estate investors are some of the most humble people I've come across and these meetup groups are usually full of enthusiastic  well intentioned people like you who are eager to meet other like minded people to share their passion with.

Not sure if tahts what caused the AC unit to work harder all this time eventaully leading to its demise.Also not sure if it helps but the PM has informed me they have sent portable AC's to the property as a temporary fix until I make a decision although I'm not sure how much time I can sit on this. in my pm contracts i typically have language that says anything over X amount we require 3 bids.

While there are many VA options and countries, I chose the Phillipines as English is their second language and there are a ton of people that are trained and familiar with real estate investing. 

It would definitely help to have some specific language in the lease they agreed to and signed before having the place cleaned and then charging them for it - especially if commenced on a recurring basis.

He spoke the language well. 

Avoid "flowery" language that just fills empty space.This isn't a social club meeting: you're speaking to a person who is probably running this like a business and has heard from a dozen other folks just like you today. 

I would speak with your contractor and ask them why they felt it was okay to commence the demo and re-roof without permits and they may be able to tell you what the scenario is.