Imagine a real crisis where they couldn't get the grid back up, and you couldn't access your accounts, etc.  

If you own either of the properties free and clear and don't need to access all of the equity to make the next purchase happen, that would be ideal.

The course heavily relies on cold calling and emailing, which hasn't been effective for me as a novice.I'm considering a different approach, such as arbitrage, as it seems more accessible for a beginner.

You could ask that they put a year or so of savings into a separate account on which you have view access or receive a monthly statement so you can see they have the ability to pay future rent.They aren't going to last without other income or savings with income at 1.25x rent.

Validate planning zoning requirements and access to utilities.

They also have a ton of resources you have access to once you sign up. 

You should not have allowed access and now you are going to live the old adage of "it's easier to give slack later than to real it in." 

If I was the originator on this loan (loan officer, lender, or whatever title is used), I would have made this restriction very clear to my borrower if they had explained that they wanted to eventually use the property as a rental.

Even though there is a tenant there now, the association could restrict or limit renters there.

Has your agent accessed the PCR within Hudhomestore to see if activating all utilities is even possible?