Why would I be cash flow negative and losing money for years and years?"

@Kash Tacke I'm a big fan of ADU's in general especially here in the mid west, yes you could potentially be on the front of the wave, but housing density is the solution to the affordability issue, anytime you are investing with affordability in mind is a great strategy to me, and sound like there are some incentives or at least supporting winds form the local city, that in itself seems like it would be worth at least approaching an architect or contractor to bid up some plans or concepts to take tot he city.  

As a couple others said emergency would negate the $500 threshold but they should contact you to notify when it happens.

Got a negative review for not having a garage to use in the winter….

I shared the concept with all of my friends, and not one of them did it.

Although whichever option you go with make sure you're also thinking about the long-term property value and what makes the most sense vs trying different angles now that negatively impact future resale/property values down the line. 

Also, focus on 2 years of job/income stability.Class D Properties:Cashflow vs Appreciation: Typically, all cashflow with little, maybe even negative, relative rent & value appreciationVacancy Est: 20%+ should be used to cover nonpayment, evictions & damages.Tenant Pool: majority will have FICO scores under 560 (almost 30% probability of default), little to no good tradelines, lots of collections & chargeoffs, recent evictions.

I know this is a differing topic on the forums, and online in general, but having the legal background/education and knowing estate planning concepts you'll realize it shouldn't be.  

You either have to earn extra money via sweat equity (working as your own PM or do the renovation work), or you have to be ok with a negative cash flow.  

This initial negative equity position consumes the initial cash flow.  2) the addition of the adu makes the property multi family and likely makes rent control apply.