You’ve even asked your bookkeeper/accountant just to get a second opinion, because after all “an accountant has to know the difference if they deal with these things every year.”

Check out this link:https://icorockies.com/event/basic-bookkeeping-rei-invest-re-via-ira-401k-workshop/?

I'm hoping to find something that streamlines our rehab scheduling, and I'm wondering if any of them also help with the bookkeeping side of it?

More bookkeeping intensive.Another layer: LLC(s) own the properties.

Does anyone have recommendations on a good property management and bookkeeping software for rentals?

Five properties isn't enough to hire a bookkeeper in my opinion. 

Down side is it makes financing more difficult, banks will still require personal guarantees on mortgages, and you will incur additional costs and book keeping with a LLC.A LLC is psychological security for those living with the fear of litigation. 

If you are paying an accountant or lawyer for services unrelated to the actual property (such as bookkeeping or drawing up blank leases, etc), then that can be expensed right away.5. 

Basically, the fees are based on whether or not the CPA also handles the book keeping\reconciliations of accounts and  they number of properties in the corporation.

When you record the deposit in your checking account, the offsetting entry is to this escrow account so that the escrow account is $0 after the deposit.Always make sure when you do your monthly bookkeeping that you your mortgage payments are broken out between principal (the loan liability) mortgage interest and escrow.