Do you suggest file 1065 or be treated as disregarded entity on schedule E. 

For Conventional, you can only use 75% of the gross rent until you have Sched E history for the rental for a net rental income analysis. 

Two of the biggest challenges I face are that I’m not very liquid at the moment, and the Seattle area is extremely expensive.

Seller has 100% responsibility for revenue production, buyer has no controls of revenue production, it impedes the operations, etc etc.. 

I know that the general guidance is that emergency funds aren't to be invested, but given our financial security and the fact that we already have a personal e-fund in a safe, non-volatile location, would it still be crazy/unwise to invest this 15k in an S&P500 index fund in a brokerage? 

Steadily has their own product (with multiple writing companies) and then they offer policies through other carriers just as an independent agency would. 

As an aside, my laundry pods for the guests and liquid for the turnovers are "free and clear" and have never gotten a complaint.I have had guests break into my owner closets, but oddly never steal (they were kids probably looking for liquor). 

And I suspect their E and O will kick in if this money is lost  just sayin..

Most rental properties in Milwaukee are old and run down, our product stands out. 

Reason being is that it allows you to invest in other products other than they offer, so that's why they don't promote these .