I don’t know the condition of the property nor how to properly assess it considering my lack of experience – who would I approach due diligence?

When dealing with unique properties like this, I would make sure that the ADU on this property is properly zoned. 

I have used Obie and Proper; I haven’t had to make a claim with either.

Things such as location, condition, aggressive rent rate, etc affect how much work may be required to properly manage a property and its tenants. 

The registration site still isn't working properly.

But it's missing a couple of integral features, such as maintenance requests/tracking, and also my bank (which I do not want to leave) for some reason has always hated connecting to Stessa and thus never works properly...

I am now looking to get the proper STR insurance on the unit.

:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

I'm big on Detroit, personally (heavily) invested there, and work with a lot of clients that wish to invest there.Homes in Detroit proper can be had for $80k - $90k today and rent for $1,200 - $1,300/mo.

Structuring your financing properly allows for sustainable growth while mitigating risks.