If I was not starting from scratch, like I did myself, I would buy SFHs because I prefer their long-term flexibility, relative scarcity, and multiple exit strategies to MFH.

STR insurance provides broader coverage, including liability, property damage (even non-guest-related), and gaps Aircover might not cover.For damages caused by guests, document everything (photos, receipts, estimates) and file a claim through Airbnb.

It should be relatively straightforward to begin discussing the goal-setting and planning process necessary to begin transitioning from current state to future state. 

For instance, said property manager manages maintenance issues, problems that arise during bookings, basically anything that needs a physical person at the property, while I manage the rest?

As far as their relation with the PM goes, the PM is the agent they used when buying the said rental, agent is local to Indianapolis, as for any form of PM agreement I do not know, it may be verbal, or they have a written agreement.Thanks in advance. 

There's a good chance the issue(s) you face has already been discussed and answered.Ask questions in the appropriate forum.

And my #1 issue is I don't see any actions to address this in a meaningful, market specific manner. 

You have a number of issues in your post unfortunately.

Maybe you can relate?

How do you think the 2 relatives will feel about having their rent raised or being required to pay rent period?