Unfortunately, some PM companies do tend to focus on bigger portfolios, leaving smaller investors feeling overlooked.

Mortar, paint & bonding materials deteriorate leaving cracks, gaps, etc. which can be concerning to look at, but this is very often addressed with repointing.

If you are not going to leave there at all, and you can't do Bill 23 or have any value-add to get to positive cash flow, then NO, don't do it. 

This forces them to leave a professional message.

Also, based on the scope you shared  it's a heavy lift to complete the work description for $45K while leaving any profit for the contractor.

Unless, you are going to leave it in the S&P 500 for a significant amount time, I would just ask why you want to invest it in the S&P 500 opposed to somewhere with less risk?

By this point, they will have already thought about what might happen if you leave, including the need to turn over the unit and find a new renter.

NY is a very tenant friendly state, so if he doesn't leave and she's on a month to month.

I signed up for the paid version of Stessa through biggerpockets only to encounter flaws in their software, connection issues that have been ongoing for 10+ months, and basic feature missing that leave me dumbfounded. 

Now I've heard they will leave it open to other bookings from Vrbo, but block other platform calendars that you have synced to yours, so they will block your Airbnb calendar for that time.