It is best to ensure you are up to the challenge before embarking down a particular path.Den Mother/Superintendent:  Our rooming house caters to International Students - we rent furnished rooms on month-to-month basis  {we do offer a term lease (academic year) or annual lease as well}.  

So I would say the next step is to file with the county and then ensure you pay your taxes.  

My bookkeeper is telling me I should just get another copy of Online (simple start) and separate my drafting from the rental.  

IMO, the foolproof way you ensure you avoid potentially squirrely irrational choices by your seller is by controlling the title, instead of a contract between you and seller.   

(about regular job, that is)You may need to take a step back and create a methodical system to ensure you are doing all you can to network, market, and grow your business.

REI is great IF:You are obsessed with new opportunities to make moneyYou're comfortable with taking big risksYou're very detail-oriented when it comes to budgetingYou've got experience in the industry (buying, selling) or you're willing to make a lot of mistakes learning itYou're willing to work a LOT to ensure that things get done correctly.Pitfalls:It can be hard to break into.

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.

Granted, we do ensure there are no pests at the time we hand off the property.

@Jason FietWelcome to BP and congrats on locating your 1st REI acquisition.However, I see some key words in your post, namely friend, money, business.Sometime they don't mix well and can even become very volatile if things are not going right.So, my suggestion would be for you to form a LLC with your friend to ensure that all business related matters are handled accordingly under one entity.Please take the extra step and time to do it right before you get started, as somewhere down the road you may be glad you did.Good luck and best wishes with your future REI activities.

I also have a bookkeeper who runs the Bookkeeping software.