Several unsuccessful attempts have been made to request payments and have received multiple excuses (could not find the checkbook or could not send electronic payment). 

Both myself and the tenants will sign the document electronically.  

If the software is not simplifying your life or making you more accurate, you shouldn't use it.Software does have extremely helpful features like online payments, marketing syndication (click a button and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

You can ask.You also need to understand the laws for direct mail (physical or electronic).

Like you, I work long hours so I outsource my PM to a team of virtual assts in Asia for $4/hr - they’re amazing & I make a ton of 💰💰💰.

If the software is not simplifying your life or making you more accurate, you shouldn't use it.Software does have extremely helpful features like online payments, marketing syndication (click a button and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

Or because of their status on the DNC all electronic communication is banned?

This is usually free if you want an electronic copy or the will charge a small fee for a printout.

If the software is not simplifying your life or making you more accurate, you shouldn't use it.Software does have extremely helpful features like online payments, marketing syndication (click a button and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

Make sure to disclose in your rental agreement that people electronically sign agreeing to on Vrbo.