Other advice I received was that I should have also placed myself as "Additional Insured" on the Borrower's insurance policy, in addition to the Mortgagee clause.

Usually this means that the tenants have to provide access (within reasonable common notice), have to cooperate in access to make repairs (if they don't they would be liable for any additional damage caused by delay in repair), and subject to paying for a locksmith because you had to change the locks because they wouldn't give keys or provide access. 

International buyers and investors bring with them additional privacy concerns, particularly around how their data is handled when it crosses jurisdictions.

This route can simplify management since you’ll only have one additional property to oversee.Multiple Properties: Splitting the funds to purchase two properties can diversify your investment portfolio.

Not sure if this is necessary but I have my own landscaping business that I work for making me self-employed or in the "S-quadrant" of "The Cashflow Quadrant".

Always prioritize protecting your interests—one misstep can lead to significant consequences, especially if someone employs a predatory attorney.

Essentially, there must be a paid parking footprint in the area already.The ideal asset would cashflow from day one with the ability to add value via technology, operations improvements, and/or NN lease addition (or renegotiation). 

Is the higher cash flow from short-term rentals worth the additional effort, or does it come with too much hassle in terms of turnover and regulations?

If you buy a fourplex, rent out three units, then live in the fourth unit and rent out the spare bedroom for additional income.

David Of course, but you have to add it to your favorites to give me a boost in the algo ;)airbnb.com/h/thevermontaframeYou can also find us at www.thevermontaframe.com which has links to direct booking, VRBO and our social media.