So, if my actual cleaning rate is $385 and I list it as $300 (and eat the difference), is this a potential tax problem down the road?

Potentially get a commercial loan or HELOC against the properties to fund additional deals.Future: I will have all the debt from the prior renovation paid off this year from the rental income.

It can be seen as a unique amenity that sets your property apart and attracts potential renters.

Joe, I can say that a lot of people avoid the West End/Portland areas, but I believe those people are short-sighted or unable to see the potential in these areas. 

If you have experience investing in this area of the country and can shed some light and insight into taxes, insurance, Airbnb options (easy/hard/impossible), permits, flooding, other potential issues, etc., I'd be most grateful!

The lenders that get a share of your property are potentially the same ones that would put into the Reno costs?

I like hi energy.

The entry-level Quickbooks Online software itself is expensive $250/yr... that's not even adding up potential books/courses, CPA fees or personal tax filing software like Turbo Tax.

A Trump win would loosen up energy policy which might mean cheaper fuel to ship goods which will trickle down to lower prices for goods, but he didn't curb spending as much as you might think.

It also sounds like you enjoyed the hosting process and the communication with your guests and potential guests when you were handling your bookings yourself.So I say why not take back control of your property's bookings, get back into the game and save yourself some money?