Some PMs and bookkeepers do this for bookkeeping purposes to more easily show the split between the income streams (same goes for late fees, laundry income, parking income, etc.).

What do you do when your book keeper gets a new job?

If your mortgage is still held by the bank, give them a call and see if they'll have any problems.Make sure that you're being diligent about your bookkeeping and let your CPA know about your plans now, not next April when you're doing your taxes.Lastly, are you sure that your home will make a good rental?

I hired an employee to handle bookkeeping and office work. 

I also get an automated email any time a deposit is made so it makes the bookkeeping easier.  

We'll be using a professional management company, so the bookkeeping side will be taken care of.

Let's say, it costs you 1.5K to get your structures in place (holding LLC or Series-LLC, with or without land trusts, with or without separate operations LLC) and 0.5K per year (for maintaining the LLC properly, bookkeeping, lawyer and CPA, etc.) for a total of 2K.

With 75-100 SF homes you should be able to hire a full time bookkeeper/property manager, handyman and sub the rest out while you quarterback the team.

I am looking for a software to help me with my property management and my bookkeeping, any advice is welcome!

I use QB for bookkeeping and I use Rentecdirect.com for webased PM software.