One more reason why people should stop looking for the easy path to building wealth.Increase earnings, reduce expenses, save, and invest.

With newer notes especially, partials reduce the discount.I'm not a fan of balloons for seller financing - especially shorter than 10 years.

Cost to build is $350K (I am managing it all myself and calling in favors around the city to get low rates on materials and labor).

They are much less restrictive than other municipalities in South Florida that are actively trying to reduce the number of STRs.Let me know if you'd like to talk further on the topic! 

Maybe half upfront and reduce the rate of interest on the balance..

Labor and Material has not depreciated in this amount of time.

Here's the City link for you to reference. https://www.chicago.gov/city/en/depts/doh/provdrs/homeowners...1) ADU regulations specifically exclude Short-Term Rentals so don't do it if the intention is to short-term rental. 2) The ceiling height oh 6'10" is almost guaranteed to trigger digging a basement if you want to formalize as an ADU unit, especially if that height is further reduced by pipes or HVAC. 3)Ingress/egress is an issue for renting, as is that any bedroom also will need two (ie operable window/doorway).

This may be controversial but it seems like you would be saving a lot of money at the moment given your reduced living costs.

Then do a thorough research on tenant applicants (note: leaving this to a PM may be hazardous to your financial health) and choose the one that is most “stable” with the best potential for long term tenancy.This advice is contrary to maximization of rental income, but IMO will reduce expenses of tenant turnover, property damage, property management fees so much that the difference in bottom line income will be quite small.  

Rehab costs and ARV (After Repair Value) are key parts of evaluating deals, so it’s great that you’re diving into these concepts early.For rehab costs, creating a rough estimate starts with understanding the scope of work and local pricing for materials and labor.