To bookkeep or not to bookkeep?

[Sterling Fields]

Hello fellow BP members! Looking for a little advice..

Little background: I am a financial analyst for a multifamily developer, so i understand real estate and all of the financials associated, but i am definitely not accountant. I currently own 7 rentals, with 2 more under contract; all are self-managed through Cozy.co.  

I am very quickly realizing that if I do not get a serious grip on this whole weekly/monthly bookkeeping thing, it could get out hand. I want to treat the properties as a business, like they should be treated(and generally do in all other areas), with weekly bookkeeping and monthly/yearly reports. 

My question is: Should I spend the time to learn an accounting software like Quicken, as well as the time imputing information weekly and keep the "books" myself? Or outsource this task to an actual bookkeeper and keep my energy focused on other aspects of the business? And also, should the bookkeeper be an online service or local firm?

My goal is to acquire another 10 units next year, and so on etc., etc. I don't plan on stopping the acquisition train anytime soon.

Any advice from investors who have faced this dilemma? What was your solution, and how did it pan-out?

Thank you so much in advance for any advice/insight!