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

@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 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.

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.

You are dealing with the issue quickly and professionally.The tenant told you the home is causing health issues.

There is almost zero chance that you bring this issue to a head and they sign a lease with a good future prospect for the tenancy.

They're usually well meaning, but when they get involved with the leasing process, a repair issue, a neighbor complaint, etc,  it always escalates the issue.

You asked about buying older properties and the biggest issues I have found is that roofs need to be replaced, HVAC needs servicing/replaced, and sometimes there are foundational issues (not super common).