Sounds like you need to get set up on some electronic payment plans for you tenants sake as well as your own...But i do get what your saying. personal accountability for your check book is lacking in our culture. 

The rent comes from the company electronically so no need to chase down rent checks. 

There are so many online tools that make it as simple as sending an email and they fill out an online application with background check, etc (cozy works well for that AND lets you collect rent electronically for free which is awesome).

You can do exactly what you already did... ask us.I am a HUD authorized Brokerage right near you and for years we have used Jordana(Dani) Angles at Central Florida Title in Clermont ([email protected]).She has over 20 years in the business and works with a number of investors.What we love is that everything can be done electronically, as we have investors as far away as Norway.

I have personally introduce myself to the tenant, explained the new payment procedure (electronic only), provided and my contact info. 

That said, there are certain things I always do, which reduce my headaches and increase guest satisfaction, such as installing electronic locks (I use YGPAK locks which are inexpensive, durable, and easy to program and use...  

I did keep and file electronically copies of all receipts as well as descriptions of all work done and materials required to complete the work.

Since I sold maintenance agreements, I touched on every aspect you mentioned above and worked with some asst living facilities. 

We had the tenant sign and then we sent the electronic copy to them. 

Everything is electronic, automated, and smooth.If the property is occupied, be prepared.