Granted, my attitude would change if I saw issues on the exterior, vacant units, etc.

Also, entitled attitudes are one reason why owners dont want to deal with certain “investors” .....  

Renters don't usually have much of a financial buffer, so they may not have the reserves to pay prior to being paid.What might be convenient for them is the ability to pay by automatic payment of some type or PayPal or some other service like that, rather than a check - in case that might be an issue.I always found that if I just sat down and talked to tenants like they were smart people who were capable of working something out with me, with an attitude of respect, it almost always worked out.So you could sit down with them and tell them that your mortgage payment is due on the 5th (or whatever), and you could possibly lose the property if you weren't paid by then, because your finances are really tight. 

And the PM played into the tenant's drama queen attitude, and when we (I became involved at this point) told them there would be no large sewer job and they were being fired - they deliberately freaked out the tenant telling them that the place was uninhabitable, trying to get the tenant to force my daughter into doing the sewer job.I went down and talked to them.

you're going to go far in this business with your attitude young man

This is the attitude, (and predicament), that I've created for myself by being far too complacent with my rental.

Personally I hate the attitude many have of serving eviction paperwork immediately on people or sending threatening documents.

I can tell we have a lot in common with your attitude though, I'll keep everyone posted!

He also has an attitude as to what he will or will not do, and which information he will or will not share, etc.

Have you had a problem before that is driving this attitude?