It needs absolutely everything separate: separate bank account, separate credit card, separate bookkeeping, separate tax ID, separate tax return.

This requires good bookkeeping and the proper formation, but is not that big of a hassle once to have it established." 

Our book keeper said their payroll was fairly easy to setup if we went back to having employees so the ease might be worth using it

Otherwise, I don't see the benefit as long as you have decent receipt tracking and book keeping practices.

I am looking at it from a bookkeeper point of view.

It keeps all book keeping together and i get my payments next day once the account has been verified

@Scott Mac"Barbers do not have to write down every clip of hair they cut and every comb they make and qualify as a cutter or a comber.CPA's do not have to write down by the minute, every thing they do during the day in a personal journal, to qualify for tax treatment as a tax consultant or a bookkeeper."

They are good with the bookkeeping and quick with their payments back to me...

You can still do your own bookkeeping throughout the year, but you need a professional to help you at tax time.Second, if all the properties are schedule E properties on your tax return, just assign the skid steer to one of the ones that is in service and take the whole deduction.

Based on the volume of work involved, you'll need a bookkeeper several days a month to be on top of the bookkeeping, reconciling accounts etc.