I like the property for a lot of reasons. 

They're hiring PMs for a reason and they fire them for not maximizing cash flow.  

You could also get a line of credit for about $150k (you should be able to borrow 75% of the value.)The reason I suggest this is…1) you save $40-$60k in selling costs. 2) you have a lower blended interest rate (2/3rds at 3.25% and 1/3rd at 7 or 8% instead of the whole $500k at 7 or 8%) saving you another $1k/mo in interest. 3) you only pay interest on that $150k when you actually use it, not from day 1  Unless you hate this property, or want to buy something you can’t afford without selling, that would be my plan.

We are looking to buy a condo in Chicago as the new rental, for a variety of reasons, but most importantly because it would rent better in the city, and it fits our desired price point (so we can allow for the rest of $$ from the sale for paying off their Oregon home and pay all, or some of the taxes on the boot). 

Main thing to watch out is DSCR Ratio.

I've flipped 6-8 houses, made good profit on those, and just purchased my first 4-unit multi for mainly cost seg purposes/long-term appreciation. 

In my experience, a successful BRRRR typically comes down to two main things: finding a good deal and managing an efficient renovation.

Have done some preliminary research and will do a deep dive, just wanted to see what folks thought of there were any obvious reasons why or why not or any markets similar that I should be considering.

Upon further review, SDHC has determined that your application remains ineligible for the following reason(s): Failure to return required forms and documents to determine eligibility   Inaccurate information/Documentation insufficient to determine eligibility  This is the Final Determination that your application for the City of San Diego COVID-19 Housing Stability Assistance Program is not eligible for assistance.

I don't know if the main participants in this discussion deserve medals or need better hobbies...