But yes, I anticipate it being a giant pain to do. 

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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.

My employer offers health care coverage but employees have to pay 100% of the premiums.

This inspection is normally just a formality looking for health and safety issues. 

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. 

Like you mentioned, 80% of our economy is based on tourism, so take a macroeconomic view on this, and all the subsidies we see in health care, construction, government jobs, low property taxes, etc. are all because they're being paid on the backs of tourists.

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

When searching for landlord-friendly areas, it's crucial to consider local regulations, tenant laws, and the overall rental market's health.