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.

Because the buyer has poor financial discipline which is why they can't qualify through a bank.If you have good financial discipline but just have bad credit due to unfortunate events outside of your control (e.g. medical issues) then my recommendation is to work hard to recover your credit and save up the funds necessary to purchase.I'm using seller-financing right now to purchase six apartments but it's because the terms are more favorable to me and the seller, not because I can't qualify through a traditional lender.

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.

Do you file lawsuits to recover damages, or do you just let the tenants get away with it?

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.