I'm kind of thinking you need to be an excellent bookkeeper or hire one if you can afford it with multiple homes...and also be very detail oriented. 

Just curious what platforms people are happy with who are managing and accounting multiple LLCS and properties.Currently using Buildium and QB but if theres a better mousetrap Id love to hear about it!!!

Up to date and knowledgeable bookkeeping will give you the raw and aggregate data points you’re looking to use.

In terms of a Book Keeper what do they actually do to provide value?

Then maybe some light bookkeeping depending how things go and I learn how my business can better benefit.Does anyone have any tips, suggestions or things to look for when working with a VA or a company that employs them?

If your portfolio is starting to overwhelm, you may want to hire a real estate-focused bookkeeper for a couple hundred bucks a month to manage this software for you. 

The bookkeeping? 

You go through fraudulent conveyance grounds, which is a different kind of lawsuit.To summarize; Land Trusts offer no more protection than a properly set up LLC, and you still have to use sane book keeping methods and stuff.

I am planning on doing my own bookkeeping, but would like to connect with someone now to establish a relationship and help determine tax saving steps before I lock things in stone.

This is because while you do have a property manager who is the landlord for rental, you still play a role in managing the overall bookkeeping, finances, taxes, insurance, and other administrative asset management tasks as the property owner.