I don’t have a problem paying a couple grand to remove some of the just figure it out stage of learning and utilizing expertise of people that already do it. 

I don't know how much you will be paying a property manager but add that in.

The OTA initially ruled against paying.

If you hire someone typically they are the ones providing this information, but if someone is paying you, then yes they need this information for tax purposes.BTW - I would say your SS# has been hacked so many times and is on the black market already this is why we monitor ours through other parties or just lock it down at experian and other agencies if you are concerned about it.

So my insurance was paying $6200 a month for "barely" furnished 2-2 apartment new the Arboretum. 

After spending 16,000 he's paying 2850.

Then invest the $10k in something that pays more than the interest you’re paying on the HELOC.  

Determine what price you can pay for the property.

If you were able to build equity over time, it could be smart to sell, pay off your loan, and use the money for another venture (flip, investments, etc) if it is truly bleeding you out.

., get a higher paying job, work two jobs, go to trade school, get a higher paying degree, live in affordable area, etc...these are things that most of us did).