I live in BC but own a duplex in Ontario, have a property manager, but the tenants on the one side I inherited with the purchase 3 years ago, and they have been a pain ever since, and below market rent too - this just may be my opportunity to get them out.

That w2 still does not limit you to things like the short term rental loophole for instance, which can help you offset those painful CA taxes.

Through door knocking and finding the sellers motivation and pain points How did you finance this deal?

Also when purchasing properties try to stay from the Historic district, each city here in Hampton Roads does have them, and the Historic Preservation Commission can be a pain to work with.  

Spent some time looking through the forums to gain further knowledge and understand some pain points to be mindful of and just to know what the community is actively doing.

As for the cheaper markets, I would look to do mid term rentals in the Rust Belt near hospitals like the Cleveland clinic to maximize the income to help mitigate the downsides and unexpected expenses associated with those markets.

Would love to learn about pain points from other property managers.So I have a career background working in software and am currently applying simply builds to common monthly tasks such as sending, receiving, and logging payments for rents.

It's a huge pain so you want to make sure you are doing things right so that you don't run into any delays.

The first 5 times will be painful and frustrating - watch one of Brandon's or David G's videos on how to run the numbers - you'll become quick after a few dry runs.Just make sure you underwrite the deals against your Goals (ROI %, Cashflow $, potential longterm appreciation, etc), and run the numbers as if you're NOT in the property. 

Usually any tenant that will be a pain will straighten out very quickly once they receive their first notice.