Best tasks for bookkeeper/assistant for self-managed Buy and Hold

[Collin Schwartz]

I have recently begun working with an individual to help me with paperwork and other tasks.

My top three tasks as of now are (after training): 

1. Paying bills and recording financials.

2. Organizing all files both digitally and with hard copies.

3. Creating written documentation on how to recreate this process (training manual).

Side Note: This individual is familiar with clerical and accounting software type of work, but not necessarily property management. 

Does anyone have any advice on areas that should be of primary focus or items to caution against?