And from what I can tell of your post, it sounds like you will lean toward being a pushover, so it will benefit you to have a hardliner first impression.I wouldn't sit at a poker table if I were you.Mine in bold.

One trick that I learned is to spell out digits instead.

Today is a digital world and most people have a smart phone and can get emails like a text message so I find it beneficial to use software that can auto email statements, receipts, notices, late payment warnings and fees. 

spend $100 on an automatic sorter and wrapper, buy the wrappers and call it a day.Royal Sovereign FS-44P 4 Row Coin Sorter with Auto Row Advancement, Digital Display and Anti-Jam Feature https://www.amazon.com/dp/B00C3WSZQY/ref=cm_sw_r_c...

Does anyone have a digital application that I can use to send to applicants?

Look at this situation like a poker wager.

When they go MTM or sign new lease I would not give option,I use Erentpayment only, I may give other option to the digitally handicapped.

I have very detailed records over more than a decade and into the triple digits in different tenants so this is not a few bad apples throwing the average off.

The key of real estate, just like poker, is to stay in the game.  

My contract states that fax, email, and digital signature would be accepted, but I'm not sure if the title company is accepting those methods