I'd love to hop on a call sometime and see if I can provide any helpful input.

If not, it may be worth it to pay them a small fee to walk through the property with you and provide their guidance/expertise.

I know you will find a ton of encouraging and helpful people here.Regarding HELOC I suggest you connect with my good friend @Michael Barbari...I believe they can still do up to 90% which is 10% more than most banks.If you need any other specific connections here in Chicago I am happy to provide them. 

Prospective residents could be required to answer customized landlord questions while also needing to provide a valid credit card prior to entry.

Section 1.165-1(b) provides that, to be allowable as a deduction under § 165(a),a loss must be evidenced by a closed and completed transaction, fixed by anidentifiable event, and, except as provided in § 165(h) and § 1.165-11, actuallysustained during the taxable year.

They are being "sold" on real estate providing so much tax benefit that it includes deduction against their regular income...

Additionally I would have countered trying to make my offer more attractive other ways - i.) waive financing contingency, ii.) show poof of funds, iii.) increase earnest money, iv.) offer to pay any short in appraisal up to a certain amount (say 1% of offer price), v.) provide a low-ball offer but with an escalation clause (you'll automatically pay X amount higher than highest bidder), vii.) say you'll pay for home as is without expecting them to fix home. 

You're providing a home, not just a house.

I really appreciate any help you can provide.

My goal is to build a portfolio that provides as much income as possible within the next 5 years, so I am thinking STR.