If you are not going to rebuild they will settle at actual cash value/market value minus the land.There are policies out there that will settle at cash-out replacement cost but they are rare and typically offered by higher end insurers for higher end owner-occupied homes.Every insurance company uses software to determine the estimated replacement cost of a home.  

You should check out conventional mortgage rates/payments vs those for DSR loans.Should also work backwards with NEW property taxes and insurance monthly amounts to determine loan amount that allows cashflow you want.

So, CPA determines that actual taxable income for the year could be as low as $85,000. 

To be determined!

The purchase price in many jurisdictions determines how the property will be taxed.

For that determination you need to ask an attorney. :)

Tax deeds are given without warranty or covenant of any type; it is the purchaser’s responsibility to determine what, if any, interest in the property is actually being purchased.

(nice to meet you.)what i can help with is determining how your property might perform as a rental. so let's do that.as you probably know, you need to factor in much more than mortgage / PITI. so:will you self-manage, or hire a PM? 

For example, software may run a report for an application, but it doesn't know how to actually evaluate the applicant and determine if they are a good fit for your rental.

The references are usually worthless but their reaction to even the request determines if they are real.