What are your daily carrying costs and how long will it take to evict them if they dig in their heels and make you go through the whole process at the end of which you're damn sure not getting a broom swept house anyway?

If I sniff out that someone is here to take advantage of the pool of new investors that find themselves sharing our space daily I go out of my way to spoil the commercial part of it for them. 

If you are focus on growing your portfolio, then use your time on more value driven task such as research, acquisitions, or capital raising, and leave the daily operations to a property manager. 

The ceilings in the basement are a hair over 7' (full size door fits), and trying to understand whether to duplex down my first floor unit and go from 3/1 to 4/2 bed/bath legally. 

Longboat does not have many daily or weekly rental properties.

And I think this is where the Midwest starts to stand out from red-haired step child of past decades to looking pretty good now.

OOS investing has been a huge headache for me, to be honest.One thing is that a property may pass an inspection but once the tenant is living there and and putting daily stress on the house,  turning on faucets and light switches, turning on heat/AC etc, thing will start to break/malfunction.

Long term rentals have the least amount of interaction required, but short term rentals (AirBnB, etc) have higher profit margins - but require a lot more attention (some companies charge 30% for management and the daily turnover service, for instance).I would suggest you compare your potential rates of return from real estate with other investment vehicles.  

As a real estate agent and an investor, I am on the market daily and explore opportunities for myself and my clients.

If rates come down a hair, it'll do absolutely nothing but hurt the economy.