I am in the middle of an introductory class to bookkeeping and highly considering taking the full class to become a professional bookkeeper.

Also when you need to get help from your bookkeeper or CPA it will be easier to get that help because they can have that quick access.

We have not looked into the 'book keeping' side of things yet in it but are going to before the next year starts.

If you have only a handful of properties making a bank account for each one and tracking all transactions for each property as separate projects in quickbooks is a simple way to handle bookkeeping, track expenses on a property by property basis, and to easily produce financials should you ever look to 1031 your properties.

I hope to get a good handle on earnings and expenses with the help of my bookkeeper and to position myself for making more purchases as soon as I am certain that my numbers will work!

Payroll, bookkeeping, etc can mostly be done remotely.Here is a great list of questions to ask a potential accountant:http://www.biggerpockets.com/forums/51/topics/70447-questions-to-ask-a-cpaAlso check out the www.NAEA.org page in your search.

There really isn't too much involved other than a little bookkeeping and scheduling of maintenance.      

Who is doing the maintenance, taking phone calls, emails, bookkeeping, showings, etc.

In either situation, you can have a property management company take the rent, do your bookkeeping, take care of the grounds and vet the renters.

If you do not like any of the property management companies in your area, you may be best off just hiring a maintenance/bookkeeper/assistant whatever makes sense.