Even if you "manage" your properties, you should have others that are doing the day to day maintenance, book keeping, evictions, etc.

As for income/expense items (capital, assets, etc), I currently do my own bookkeeping, so I have reviewed the IRS documents pertaining to rentals and deductions and such.

Will help you save for the income property while getting used to 'dealing' with a tenant and getting used to the bookkeeping and tax side of things as well.

Once I close on a multifamily property, what are the key operational tools needed for bookkeeping, rent collection, tentant screening, maintenance scheduling, etc., that I need in place in order to "keep the lights on"?

@Vitalii LunkoI use Excel for my bookkeeping, and MS Project to document my tasks. 

I feel like it would help my accountant out and cut the book keeping costs down opposed to handing him a stack of receipts & statements. 

There are tax accountants, bookkeepers, financial advisers, transactional service consultants, etc. 

Ideally, the CPA does bookkeeping as well.In regard to legal costs, it varies from attorney-to-attorney.

The plan is to manage a few properties myself to get my systems in place then hire someone to do showings/book keeping on the software,I know this will be a constant work in progress and I will adjust things as I go but 2 things I want to get strait before I start...Legal - I have reviewed fair housing laws and will have my employee do the same - but incase legal issue/questions or evictions come up should I contact an attorney now?

I think you got your answers above but I do recommend the book.  Keep