The first being that it is simple and more orderly from a bookkeeping/accounting perspective as it will be separate from my flips.

Has anybody had luck with a VA (virtual assistant) with bookkeeping for their real estate investments?

The commercial space is about 300 sqft and is currently being used as a bookkeeping/accounting office with no foot traffic.The policy I currently have is threatening to jack up my rates so I'm looking for some other options. 

From these resources, I've learned that I need to build a team that includes a realtor, contractor, CPA, bookkeeper, lender, mentor, property manager, etc. 

This is  pretty much bookkeeping 101, if you're going to be in business, treat it like a business. :)

@John UnderwoodHow does the bookkeeping work for that??

I use Staggs Consulting for bookkeeping and they are great and if they can't do your taxes they are happy to refer you!

LLC's are also about order and ease of bookkeeping.

But, is it worth it to you have pay the higher lending costs, more tax filings, more bookkeeping/accounting (remember each LLC will need its own bank account), whatever yearly (usually ~$100) State registration fee, and whatever state/local laws for the limited liability protection of the legal entity?

Or you can hire a book-keeper and send scans/photos of receipts to them.