As they are getting paid to provide a service.

I did a "blind" assessment where I paid/reimbursed a close family friend to go in as a guest because there were a lot of details I wasn't privy to- and wanted to understand (the whole experience and process from the guest perspective from the initial inquiry, emails, etc.).They shared the email communications (some of which was glitchy or not quite as good as what I'd expect, or told me of delays in receiving responses).

At the end of the day, 99% of sellers and brokers only care about your surety to close (I leave out 1% that might care about HOW you operate your deals, regardless of price paid).The fact that you have never closed a large transaction AND are not providing all your proof of funds up front and/or talking with brokers about where the money is coming from, will give them some trepidation.  

Private loan that I paid when the sale was finalized.

It's understandable to think a paid off property will "make more $" but it's just not true.

The title company cannot find a release for the loan from 1998 and says they need proof from the seller that it was paid.

Private loan that I paid when the sale was finalized.

That kind of errand is not the sort of thing they are paid to do and our liaison wasn't able to devote enough time to the problem on a daily basis to make it happen which I completely understood but it was still frustrating. 

If I had to guess I would say your money could “develop” 1-2 houses in Staten Island but in the right market you could easily get up to 12 or possibly more good units fully paid for.

However, if I sell I won’t have to pay out of pocket, in my 2.5 years I have paid down and my property has appreciated enough so that after all repairs the realtor estimates I’ll make 50k.