While I did spend about $15K on renovations, that amount doesn't need to be factored in for this discussion.

Yes if you hold it long term (really long term), you may get back the same amount that you would have received by not paying capital gains, but you have to hold it long term AND have the house appreciate. 

The company offers promissory notes worth $50k, $100k, and $200k+, with annual interest rates ranging between 12% and 16.7% depending on the investment amount.

Looking to limit the amount of cash I need to put in (ideally under $10k) by leveraging different financing options @Eric Huntermark I think less than $10k down on a purchase price of $150k is going to be hard to find.

If the leases end up in the realm of where we believe they will the value of the building will go up a good amount and we will have close to 1 million in equity.  

I suspect there would be massive blow back if the feds attempt to lower sec 8 rental assistance. 

Regarding BRRRing OOS - it can be very dangerous:(Too many newbies take contractors and agents at their word, when "trust, but verify" is extremely important.Given you're in Chicago, would recommend you plan 2 trips for a BRRRR:1) Initial walk-thru with contractor(s), which you should video for documentation & accountability.2) Final walk-thru BEFORE paying out final amounts to contractor(s). 

I pay for prop stream and love the amount of detail you can add into a search. 

However, I have a good amount of friends who have made WA work very well for them.

And the amount of cash invested suggests you got a conventional, residential loan that allows you to house hack, is that accurate?