Is it worthwhile opening a discussion with the property owner to see if they're open to selling the property?

You've shared so many gems and described a realistic depiction of purchasing an investment property. 

That's why you see so much trapped equity in properties owners cannot access. 

I would suggest you hire an inspector as well as have a general contractor go out to the property.

There are limited exemptions such as if you inherited the property where it would be allowed.There are technical means to navigate the 90 day rule but your best bet by far is to talk to the lender and let them know the situation and ask for their direct guidance.  

Whether it be cleaning their properties or doing manual labor.

Your property manager4.

Wow looks like a beautiful property!!

It will NOT be an A/B class property. 

I've already had a home inspection done and it basically told me what I already knew about the property.