Files can be shared in the cloud with bank level encryption.

If you do send them 1099s via email – use passwords and encryption or remove the SSN.Who should receive 1099-NEC?

I could easily train virtual assistants to handle these payments and have an app created for encrypting sensitive data for facilitating the transactions through financial service partners from my main line of business.

If you connect your bank and other financial accounts, the connection should be encrypted.

New privacy laws demand that these platforms have robust consent management mechanisms, data encryption, and audit trails in place.

All data transferred within TenantCloud is encrypted.

As I have never seen a self-managing person using a secured server service on e-mail security, encryption etc..

You will see very lengthy and almost encrypted listings but once you know what you are looking for the rest is easy. 

You could also ask the bookkeeper which CPA does he/she collaborate with and then verify the competence level with with the CPA.If you are concerned about the safety of your financial documents, most cloud based accountants use software (Quickbooks, file sharing services, etc) with bank-level encryption. 

I then save or scan everything to an encrypted drive and shred any paper.