Or does property management give you a better picture of the back end tasks and more of the everyday operations of how a property makes you money?

Your thoughts seem to be spot on with my own thinking as I launch this new adventure in my family's lives.

should I find a CPA to do this specific task every quarter/annually ? 

You may want to look into a system where you pay them after they get certain tasks completed.

What is the best way to start the adventure I am looking to go on?

Where you are weak or have tasks you don't like/want to do, your partner should be skilled at those areas, vice versa. 

I have been on a path to break the mentality of past generations and journey to freedom to provide the same opportunity for others, I understand a business requires people who are more intelligent then I doing specialized tasks such as an Accountant, CPA and a Broker.

I'm not exactly sure where is a hot place for rentals at the moment without it breaking the bank, I know that can be a tall task with the market we are in.

Seems like a small task.

@Arman A. my vote is:Option 2 - Sell the place and buy two properties possibly a duplex.I say this because if this is your principal residence you can avoid capital gains taxes.However, if you are looking to buy two properties in California, that might be a difficult task.