Black Swan- there are a lot of potential economic hits right now. 

Saw the potential to add value to this tired property without making a significant investment in time and money How did you find this deal and how did you negotiate it?

However, it might also incur additional accounting and tax complexities.Non-Real Assets:Holding Company: If the non-real assets are essential to the operation of the property, holding them in the same company as the property (either operating or holding) makes sense for financial reporting purposes.Separate Entity: If these non-real assets are more independent or potentially have different risk profiles, consider holding them in a separate entity owned by the holding company.

It makes me wonder if I should pull the mortgage anyway and take the potential liability risk.

We have not yet reached our full cashflow or market value potential, and likely will not for another year (as most tenants are now in 1y leases expiring again in Dec), but we are in amazing shape with this value-add process.”For context, the ‘day one’ true net cashflow for this property was about $800/mo, and the full true net cashflow potential with market rents is just over $6,000/mo.

I bet everything I had and made the owner a good offer.

I mean look at what happened in Bend Or. and Wenatchee has 5X the potential of Bend.. other than Bend has a better ski mountain. 

The best idea I have is for a vetting service renters can use to screen potential rentals/landlords.

If you have a STR that self-manage, you may potentially be able to treat it as 'active' instead of 'passive' which would allow you to offset the losses against the other forms of income such as wages, interest and dividends.You may accelerate the paper-losses by doing a cost segregation study.

The potential here is significantly higher and since the price point is higher, now my 5% appreciation is more as well.