That ensures that the IRS will get some taxation benefit from the sale. 

How would this be declared/explained to the IRS...or is this in any shape or form prohibited?

My question is... what specific part of the analysis should I be focusing on to determine if it’s a good deal.

Base your new offer on the value you have determined once inspected paperwork and property.

An agent can run a CMA for you and determine this price. 

Once you have determined your outgoing expenses and communicated a budget to your significant, I will move to your housing situation.

Some things to consider now, before you actually start investing, is to determine what type of investing you think you'd want to do (Rental Property vs House-hack, Fix & Flip, vs Airbnb, vs Wholesaling).

Provide your w-2 2019 2020, IRS returns, paycheck stub, last month bank statements and the target amount you desire, type of property, condition of property, vesting

It's important to note that while most liens are wiped out from a tax sale, there are some liens that survive. 1) IRS Liens2) Water and Utility LiensMost important is to understand any right of redemption period.

What’s your rule of thumb for determining how much you will pay for land/lots?