I have requested e-signature to be added as a feature for my leases. 

There is a chance you do not possess paperwork from that long ago, in which case hopefully the former employer still exists and has records, you can also request tax returns transcripts from the IRS website or by filling out paperwork and mailing it in.Interestingly, banks don't do comprehensive criminal background checks (just for financial crimes specifically, though I've never personally worked on a loan where that came up, guess I'm not on the Wolf of Wall Street's speed dial).

After that you can convert it to a rental without requesting anyone's approval or doing any mortgage paperwork.

I had not thought about calling the local water authority and requesting previous water bills.

@Joe Delgrosso I've always been told it automatically drops at 22% but you can submit a written request at 20% to have it removed.

I came across the SILA website (http://www.skokielandlord.org/) and requested membership but so far have not gotten any response back.

This past fall I had an offer verbally accepted (email) with a request to increase my EMD.

As requested (yes I read to the end), I will share my goals for 2020.

Examples: I take a refundable pet deposit instead of a non-refundable one or a monthly fee, I currently pay the whole water bill without taking money from tenants because the duplex is watered together (I will eventually get a separate meter but the outlay is more than I want to pay right now) assuming it doesn't get out of control, paid for the new doorknobs on the bedrooms because the tenants requested locks despite the lead tenant saying they would pay for it, planning to replace the microwave hood simply because it's louder than it should be though it still works, etc.I'm probably losing out on a minimum of $100 monthly.

Buyer agrees to verify the above representation upon the reasonable request of Seller and to authorize the disclosure of such financial information to Seller, Seller’s attorney or Seller’s broker that may be reasonably necessary to prove the availability of sufficient funds to close.