You also need an accountant to help both understand the bookkeeping and tax requirements for your business.

Isn't this basically what bookkeepers and accountants are already doing?

This made the most sense for us with a growing family and our local housing market.I have a few questions about the accounting/bookkeeping side.

Another suggestion is to do bookkeeping monthly, leverage automatic transaction importing, automatic tagging as much as you can. 

I suppose....but someone that understands the bookkeeping for RE.

They're great at what they do, but book keeping, invoicing, maintaining a schedule, communication, and other vital business skills are lacking.

This platform is called account management and basically eliminates my bookkeeper.

It saves time because there is not double-entry of bookkeeping: pulling data from PayPal and then having to port it into software that tracks the financials of the rental properties.I have a lot of client for whom we only do the bookkeeping.  

Let's say, it costs you 1.5K to get your structures in place (holding LLC or Series-LLC, with or without land trusts, with or without separate operations LLC)  and 0.5K per year (for maintaining the LLC properly, bookkeeping, lawyer and CPA, etc.) for a total of 2K.

Drafting resolutions for each transaction, corporate minutes, annual meetings, maintaining separate bank accounts and bookkeeping for each entity, tax preparation, franchise taxes filing and payments... the list goes on and on.