Because I needed to track expenses in various ways (across both properties and two different schedule C incomes), I had to use what Quickbooks calls "properties," "classes," and "projects," and using all of these bumped me into the highest and most expensive tier, currently $970/year with the annual payment discount.

If not why would you let them buy a completely flipped property at a discount. 

They are inside (above) backyard at 25% inside property line back fence.Personally I would not buy it to stay permanently as primary (don't mind to stay year or two as tenant) but it is for investment and I can get some discount for this reason.

If it's a newer company,  and projected to grow, you might consider their projected discounted cash flows to evaluate the company.

Insert worst place to get a home value (zillow, realtor, tax value)  says the house is worth X, how much of a discount should I offer off that?

Perhaps offer a discount for booking well in advance.   

It likely has never been closer to having funding that can significantly improve the situation, but it is still a ways from being a reality (but once the problem is resolved, the discount due to the issue will quickly vanish). 

The only thing I would say is that the east side neighborhoods(Dignowty, Highland Park, Government Hill, etc..) are getting nicer every month since there are so many investors rehabbing those properties, so I wouldn't discount them completely.

You will have to buy at a very deep discount since your rate will be very high.I follow that guy as well, and it does look like he does good work. 

Most investors I talk to focus too much on discounting the sales price to squeeze as much as they can from a seller.