The initial tenant issue was settled at $700 and change, which I paid.

If you are "cured" of your analysis paralysis and have the capacity to stomach the project and the "issues" that come with it, I vote BRRRR.  

I want a good business that also solves some housing shortage issues.

I still want to get them to come over to website and get on a list, so I can educate them on certain housing and real estate issues.

The wholesaler won't disclose any issues that the property has that could prevent them from getting paid.

I've been using it for over 4 years for self showings with no issues.

@Andrew Caton if money isn't an issue you should have no problem getting approved by a bank, it would probably be harder to get two unrelated people approved for a single loan than it would for you to get approved on your own. 

I’m not so concerned with how to turn them on, it’s more what immediate issues may I encounter when doing so and how can I mitigate them.

For a scope like yours, it typically takes 2-3 months with a solid GC, though sometimes supply issues can stretch that out.

We're currently looking for ways to streamline supplies for cleaners (toiletries, towels, item replacements) and handle small handyman issues.