What drew me to Detroit initially was the potential for strong cash flow, but I’ve also seen appreciation in several of my properties as the city continues to improve.

Security systems are easily outsmarted, that’s the point of the initial visit, to case the joint. 

I’ve often seen this happen where initial approval is given, but debt-to-income issues arise once they discover you’re purchasing another property.

The structure of the business is changing behind the scenes, but the ownership of the accounts by the business remains the same.IE if the guy who created the "Vacasa" account on Airbnb/VRBO leaves Vacasa, they don't have to start over with a new account just because the guy that initially created the accounts left. 

Screening tenants is initially Padsplit. 

I initiated the eviction process when the tenant was two months behind on payments.

I stumbled upon this thread and I'll admin I've only just read your initial post.

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.  

If you had identified the property, the cost and the travel cost would have been added to the basis of the property and depreciated.These initial investigatory costs are treated differently for flipping and rentals.1) Flipping: The travel cost to investigate will be treated as a business cost and deducted as an ordinary travel cost.

Once you get past the initial learning curve and have some basic knowledge, it gets a lot easier though and at that point most knowledge gaps can be filled as they come up.