At a minimum, I believe they have a grip on the average days per home. 

I had to slash prices to get any bookings and then it makes it not financially worthwhile since it’s occupying a great deal of my time to manage (obviously the time investment will dwindle once I get a better grip on managing a STR) and dealing with turnover and weird people and guests on Airbnb is not something I’m a fan of.

I have gotten a basic grip on most markets.

It may be your accountant doesn't have a firm grip on RE accounting requirements, he may not want to mess with it, you might ask him some other time if he has RE investors as clients, if not, there is his reason most likely.

Most landlords try to work it out with me, usually quite unsatisfactorily, but I still give the opportunity for them to come to grips with the fact they've crossed a great tenant.

If I was gifted one million dollars, I would offer my capital as incentive to partner with the most accomplished real estate flipper I could find in exchange for the opportunity to learn from the partner and split profits 50/50.Once I had a firm grip of how to identify, act on, and execute a flip, I would use the original money and gains to invest in several single family homes that needed rehabbed.

The front steps have no grip/texture and the gutters drip onto them and it becomes a sheet of ice. 

You could try a few things that might help get a grip on the situation a little better.

Having multi-family property in (or near) a city like Portland, in the grips of a housing shortage, isn't a bad thing. 

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