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. 

For instance, our company handles all the administration, compliance and bookkeeping work for your investments so you don't need to constantly deal with that as you would in a Checkbook IRA.

I could not imagine doing this for 40 seperate units.It seems this would be a bookkeeping nightmare for me.Is anyone using this type of asset protection strategy for 5+ properties?

Put some systems into place with bookkeeping, maintenance, forms, etc. and learn what your state/county/city requires of landlords.