Things can and will go bad, but once there is enough monthly cash flow generated it will be extremely difficult for that one big issue to put us away or even 2-3 big issues all at once. 

The PM is slacking and poorly addressing tenant issues. 

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.

A lot of maintenance issues are repeated again and again on all the properties a PMC manages.So, a PMC has pretty good idea of what many issues cost.

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

You have a number of issues in your post unfortunately.

The issue is our land value is high, so the structure value is low compared to the overall property cost. 

It separates your personal assets from your business, providing a safeguard if any legal issues arise related to tenants or the property.

There are cheaper one’s in D/F areas but I would be careful as those can create a laundry list of additional issues.

I’m interested in purchasing an investment property with equity I’ve developed in my current home, however I’m concerned that if I have an issue renting out the new home it can blow up in my face.