Going with a generalist or some random CPA may be more feasible, but it's more feasible for a reason.

So really I just need accounting software which tracks various assets, my basis in those assets, and gain/loss when I sell.I have used Quicken for many years but upgraded a year ago to Quickbooks for one of my entities just as an experiment.  

Overpriced, crappy areas, no exit without a loss and less than accurate numbers presented is why.

I m projecting a sale and a big loss.

, other investments (do I have passive income, as well, providing me with passive losses?)

If you have a buy and hold rental and if you are doing your taxes right, you should have a net loss on your rental and owe no taxes.Let me know if I can help.

I'd like opinions on your strategy for balancing monthly cost with overall risk of loss.2) How do rental property insurance and renter's insurance overlap?

The student LOSES money, and the teacher has to share the loss as well.Mathematically the former is OK because neither the student nor teacher has that much risk, but if there are N students that wanted a refund and the educator spent let's say 10 hours with them then the teacher has wasted 10 hours of their time, but the students collective lost N * 10 hours of their time.

The last thing I will add is I think it's worth factoring in that from Charlotte (or Apex in your case), the feasibility of using the property during some of the open calendar dates has a value, and should be taken into consideration. 

ACV polices will list 8 or so types of loss that will be covered by the policy and if it’s not named...it’s NOT covered.RCV polices are an “all risk” type of policy so it will only list the exceptions that are not covered - as long as the loss isn’t listed as an exception than it will be covered.It’s complicated and is why some people hate the concept of insurance because they end up learning this stuff as part of filing their first claim.