This could be just specific to the real estate industry, but in both recruiting and cybersecurity consultants (hackers for hire), the ones that start their own business/consultancy, are the ones who after spending 2 years (usually exactly 2 years which is when recruiters will message them), the high performer will either 1.

How can we prove that any damage is caused by this specific tenant, given multiple residents in the property?

You'll lose rent while property is vacant, and you'll probably have to do more repairs to attract a new tenant than you would to keep the current tenant.Is all that worth requiring a tenant to use one specific payment platform?

I did not want to simply rely on one source so I figured there are people here that would be up-to-date if such a manner was so as well. 

We also love podcasts so if any specific episode of the BP shows come to mind let me know! 

So, the first question they usually ask a PMC is about fees - instead of asking about services and HOW those services are executed.EXAMPLE: PMC states they will handle tenant screening – what does that specifically mean?

Quote from @Emily Gowen: I only recommend investors sell when they can move the money to a better-performing investment or when the sale moves them closer to a specific goal.

You might consider other strategies, like taking a home equity loan or refinancing to fund repairs, but consulting with a tax professional or CPA would be the best next step for your specific situation. 

Have proof on hand (easy enough to find) online of the missed tax payments and any documentation that supports that he specifically didn't pay his taxes.Probably a simply mistake on his part, but now if he wants to develop on it, he either has to land lease it from you or buy it back.I'm not sure how the whole tax deed thing works, so that would be something you have to figure out between the two of you.

That said, there are alternative ways to meet the requirements, and with proper planning, you might not need to rely on these specific tests if most or all of the participation comes from you during the first year.