A typical policy for short term rentals is going to cover most, if not all, of the perils you have listed.But if it is a homeowner's policy or standard landlord policy, the insurer may well deny claims, since the property is being used differently than what is described in the policy. 

Any advice is welcome.Are you going to live in one of the units, or is this investment only?

If you are going to put alot down it would work, or check their latest requirements.  

Quote from @Robel Nessro: How is President Trump going to effect the Real Estate Industry, will it benefit the investors or impact the market and investors?  

I've found that if you're going to do section 8, a lot of your trust is in the property manager to make or break the deal.

I thought it is still going, especially if one has already created the fund, but I will check because I could be wrong.

They knew all along they weren't going to fund this flip.

There have been some very good spreadsheets posted on here in the past that you can search for and find.A spreadsheet is going to be much easier to use and play with different numbers than an app.

Can you count that $4,600 as “rental income” or does it have to go under some kind of self employment?

What type of strategy are you going after?