Quote from @Matthew Cook: Dig into those comps with a realtor doing business in that market.

Due to the nature of the shorter lease terms, I am spending an excessive amount of time updating my Excel spreadsheet, MLS, business website, Airbnb, VRBO, and other platforms.

I'm the sole manager of the business and the properties.

A personal liability policy "MAY" extend to one or two rentals but if you are planning on building a portfolio consider the commercial umbrella.Another thing to consider is that the courts frown on carry high personal liability but low business liability when trying to hide behind the vail.

PMs are busy - if you email a PM and say "Hey PM, I'm looking at 123 Main St. and I think it will rent for $1500 a month, does that sounds right?"

S8 is the business of last resort.

I figure this would be really helpful for anyone in our business.

For example, it is not unusual for me and my business partner to buy 4-unit buildings for about $250k and be able to rent them out for $4,000+/mo. 

From there, it requires the ability to conduct underwriting the highest and best use of a planned project, which requires a pro forma built by the user or acquired from a competent 3rd party. 

If you find a solid, boots on the ground realtor/PM who has experience in the flip business you should be fine.