Your main issues will be eggress, as usual in a basement.

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.

Now I can see some builders having an issue with comps.. but other than that its crazy to take these funds as income and then pay tax and plow it right back in.. 

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.

It does however give you a degree of independence to choose what you want to do.As your portfolio grows you'll also feel the weight of future capex responsibility more, which ironically points you to growing more cash flow through more real estate.The other issue is that you are chasing a moving goalpost.

She’s currently not paying rent, and while she has some health issues and no stable income, she’s been communicative and open to general talks, with a possible option to vacate through a cash-for-keys arrangement, though this might take around six weeks and some hard work.I plan to rehab the property and eventually rent it out, potentially to a Section 8 tenant.

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. 

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

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