It seems to me that one owner owning that many units means I only have to go to one person to chase down a lot payment.

Somethings that I consider: ROI (cash flow) - This is the obvious one but definitely isn't my end all and that's gotten me in some trouble chasing high returns in rough neighborhoods.Distance - Being a remote investor, I prefer to have a certain level of access.   

Is there any other way I should chase money or better career?

Unfortunately retail banks wells, chase, BofA will not work with you at all.  

I am just saying sometimes and most times for these tiny dollars simply the cost of doing business if you cant afford to lose 500.00 you should not be buying rental real estate in the first place.. but i hear ya its like clients that I know that are land lords that will go to the end of the earth to chase tenants for a month or two of rent.. again in my mind a total waste of time and effort and emotion.. and just cost of doing business.. unless of course your a debt collector by trade  :)I would no way want to be in your position.. when you make the final call on who gets EMD your making one person happy and totally pissing off and losing a client most likely on the other side.. 

I wonder at this point if going to apply for another loan, like the one you mentioned with FHA, is gonna do me harm with my previous loan approval from Chase.

If it needed a new septic system that would be an additional $20K There were eight bidders chasing this deal!    

I've talked directly to bankers at Chase, Wells, and somebody experienced at Cushman Wakefield who is a loan broker.  

Time and time again we hear that Absentee landlords, Probate leads and Evictions are some of the best leads to chase.

The long answer can make you chase your tail for ages and never invest--analysis paralysis.