If they are just messy and unorganized, you can insist that the property be kept to a certain standard and if they don't want to move they must comply or you evict them.

I had a landlord once who insisted on picking up the rent every month, and it did make me feel like he didn't trust me. 

Insist on references from other owners in your market. 

The job is so much easier when you set your rules and insist they be followed.

If it were, they'd take my donation without insisting on a cash payment.

The worst case scenario is you purchase a house for too high a price, end up hiring the wrong contractors, they rip you off by overcharging, insisting upon advances and by doing shoddy work -- and you can't refi in even nine months because the house is still a construction zone -- and you ask him for yet more money so you can finish and try to get him back something. 

Such as insisting on mailed forms, mailed checks and and only doing approvals once a month. 

I too believe that the best choice of action would be to alert his competition or hire an outside force, but my father insists he would rather not add to the stress of the situation. in the end id say with this many problems id rather lose the problem all together as well.

----->>> what's even worse and an even bigger red flag is when they insist on signing the lease TODAY! 

Insurance agent insists this is the only way he can do it.