We simply didn't know that we were communicating with each other due to Craigslist's encrypted email system. 

I'm under the old school approach of meeting and sitting down with a CPA as opposed to submitting sensitive information via e-mail to an accountant regardless of whether it can be highly encrypted.

Google Drive is great, but I'm reluctance to store some documents on the cloud, and for the documents that I do, I use AXCrypt to encrypt everything with at least a 16 character key.

You won't get the right skillset.I use LastPass to send them passwords that are encrypted so they cannot see my passwords but can access my sites.

Hi @Maroun Youness.Orders are SSL encrypted.

One plus side I see with this is that social security numbers are encrypted - so tenants aren't as weary about providing that information. 

If the information contained in the documents is sensitive, the files are secure, but you may be best to add an encryption program on both ends to fully secure them to your level of comfort.

Tiller uses Yodlee to handle encrypted logins, maybe their connection to banking data is more robust than Stessa's free version. 

Craigslist encrypts your email and when ad appears they don't see your email.

Is it encrypted?