Cash invested: $80,000 Acquired this property Sub-to as a quick flip with minimal repairs required.

Chicago would also require a $0 exempt stamp,Just a FYI, Any deed recorded in Chicago will require a City of Chicago water cert.Directly from my title guy.But like John said your attorney should be able to tell you exactly.

Just be cautious of DTI (debt-to-income) ratios when qualifying for additional loans if you’re relying on projected STR income—most lenders require at least 12 months of rental history.

If it was me...I'd check with zoning to find out how many dwelling units I could build, and I'd find what the requirements are for those units (type of house, height and setback restrictions, etc.).Then I'd find out what local builders think the cost to construct would be - just get a cost estimate per square foot for 2 or 3 different levels of finish.

Is it required to have a brokers license or be listed under someone that does? 

It's critically important to make sure you know the exact zoning in regards to minimum stay requirements before you go too deep into a property.

After I reached that goal, I set a new goal of 3x the required income for financial independence with the intent of giving 2/3 of it to charity.I don't believe in leaving a massive legacy for my children.

I can come up with only about a third of the required down payment. 

Deduct NEW property taxes after you buyDeduct home insurance costsDeduct maintenance percentage, typically 10%Deduct vacancy+tenant nonperformance percentage(we recommend 5% for Class A, 10% Class B, 20% Class C, good luck with Class D)Deduct whatever dollar/percentage of cashflow you wantNow, what you have left over is the amount for debt service.Enter it into a mortgage calculator, with current interest rate for an investment property, to determine your maximum mortgage amount.Divide the mortgage amount by either 75% or 80%, depending on the required down payment percentage - this is your tentative price to offer.If the property needs repairs, you'll want to deduct 110%-120% of the estimated repairs from this amount.Be sure to also research the ARV and make sure it's 10-20% higher than your tentative purchase price.As long as the ARV checks out, this is the purchase price to offer.It is probably significantly below the asking price.

Just looking at their website,  there is no useful or helpful information that a sophisticated investor would normally require (to even give them a chance of being considered).