You should be able to buy a 3 flat for that all day long all your numbers will be better. 

Ultimately, He would like to stay and live in the “granny flat” or Ohana unit and be a “house manager” for the property.Are there any creative suggestions people might have in how I can help him and seize on an opportunity?

As far as I know, there are flat fees, and percentage fees for them.

I'm the Chicago suburbs, but a downtown 3-flat (Chicago is weird and calls 3 units a 3flat instead of a triplex) in an A+ neighborhood like Lincoln Park or Wrigleyville will never cashflowMy wife and I even looked at a couple that could be used as an owner-occupant and the rent from the other units don't offset the mortgage.

In our market the property prices rose significantly in 2020, but rents were flat. 

@Aj Parikh but shouldn’t I use this time to maybe reposition the portfolio toward newer and higher growth neighborhoods while the market is hot given the flat rent growth and other tenant quality aspects?

I actually just posted this in another thread, but what I have found that works for us is:YourPorter + PriceLabsI initially chose PriceLabs because it is the only pricing software that is a flat rate rather than % of your revenue.

If the owner doesn't know how to sell without a realtor you could agree on a price and have a lawyer or a flat fee realtor complete the tar 1-4 contact (its online and you need to read it) for you guys.

I was just going to do a flat rate for the whole lease, but it seems more cost effective doing a calculation per month.

Contacts - I learned about the process with the help of several local contacts - my landlord/mentor/surf buddy that I was renting from when we first arrive in Peru provided encouragement and other connections such as a local lawyer we hired for a flat fee - this was piece of mind as we were ultimately going to sign contracts completely in Spanish!