Wholesaling is desirable because it requires the least financial commitment and can help you build money for your other investments, such as rentals.

I decide its best to cut my losses now because I'm not going to be able to fix this issue to his desire and give them a 30 day notice to vacate.

Just because somebody says or does a certain thing doesn't mean we have to agree or like it but there is always value to be had in everything if you desire to see, hear or find it!

We can decide to lower weeknights accordingly, if desired. 

I am not a landlord so does not affect me.. and it has made the MF in the neighboring burgs that much more desirable.. but I think its NOT quite as onerous .. you can raise the rent 10% a year without penalty and renters tend to stay much longer in this market than the cash flow markets.. and there is little to NO section 8 its all market rent with 700 ficos and real income LOL

He has absolutely no desire to manage real estate or be involved with any of the headaches that come along with searching for properties, rehabs, etc.

Don't hate on the tenant applicants that, like you, enjoy being their own boss and setting their own hours, provided that this desire isn't getting in the way of steady/increasing income. :)If they are dodgy about showing this stuff, or want you to focus on some future projection they've created in Excel or via a guru framework (yup, the taxi alternatives have taxi gurus just like we have RE and airbnb gurus!)

I'm going to throw my opinion and real life observations out there, please consider it my view of the world as it is, not as I want it to be...15-20 years ago the easiest way to get ahead of the gentrification curve was to follow the artists and homosexual couples into the less desirable neighborhoods.  

If it is in somewhat of a desirable area I wouldn't even think twice about denying either of these applicants.Red FlagsApplicant 1: Slow in getting you back background check, the collection amount for the mom is very high. 

It could be experience, manpower, competitiveness, quality of employees, desire, and many other issues that will make a difference in management companies.