I’m always happy to connect and chat if you need anything we also host 7 free meetups a month in MA, NH, and ME, we have one in Portsmouth, all under the name “Simplified REI” they’re posted here on BP on the Events tab along with many other local meetups.

Ideally, you use a master key or keypad system to simplify things going forward. 2.

(Cozy.co won't work because they require the tenant to have a checking account.)Here's a link to a similar (and very long) thread on this same topic that might be helpful: https://www.biggerpockets.com/forums/52/topics/222243-paying-rent-with-cash---simplifying-processes

Also is there some sort of simplified contractual document that I could use to secure my interest in the property if she was interested?

They cost just a few dollars per tenant per month usually, and it simplifies a lot of your tasks.

Can't share phone numbers here, but Google local insurance broker, Simplified Insurance.

Yes you are right Charles, thanks for simplifying the question. 

If you have enough doors you can get a commercial blanket policy.Otherwise, individual policies will depend on location and condition.Contact Simplified Insurance.

These simplified scenarios aim to illustrate the potential benefits.

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.