Administrative (do you need a book-keeper, attorney, CPA, etc?)

I also am fairly good at personal bookkeeping so I feel like I can generate my own personal cash flow statement.

I don't see debt and credit or double entry bookkeeping whereas there is accrual accounting.

Hello @Chris Pomerleau, we use Quickbooks because our CPA and bookkeeper who focus their business on real estate investors, use it and I would strongly suggest you do the same.  

We are also currently trying to find a more robust program, specifically for better accounting.As we are considering using Buildium for our rental properties, can you please elaborate on the nature of the issue with displaying trial balances and other accounting shortfalls, so our bookkeeper can know if it'll be a dealbreaker?

I have had that discussion with my CPA and bookkeeper and I plan on doing exactly that for the care home I am getting started.

I have heard there is a service that some bookkeepers and maybe some accounts offer to setup your Quickbooks for rentals at the very start so you know it is done correctly and then hand it off to you to maintain.

A 25% return with the headache of buying, managing, bookkeeping, conversations with lenders/PM/tenants/repairmen.. no thanks.

I've got a full time book keeper and i feel like buildium is asking me to do too much work. 

You don't need a bookkeeper.