Whether you need a CPA with just three rentals depends on the complexity of your situation and your comfort level with DIY tax prep.If things are pretty straightforward, you might be fine with tax software for now.

No one's perfect and honest mistakes happen and a PMC often needs guidance as to what level an owners wants to maintain their property.Wasn't trying to solicit your business,so I'll respond via DM about the rest of your questions:)

The lot is flat and level, so we only need a short gravel driveway.

High level local impacts are rising rents from Santa Barbara to San Diego and high demand for luxury purchases.

For example, the stairway is not level and you would have to scrap the house and rebuild to live here.

From using data to identify emerging markets to building tools that automate property analysis or management, your skills could really give you an edge.

If they work and the risk level is something you are comfortable with, go for it.

THEY ARE STEALING FROM YOU (remember your remark about him not even getting a fast food/entry level job? 

Quote from @Jonathan Grzeszczyk: David Greene has a series (Sold, Skilled, Scale) that teaches agents how to run their business like a business.

The answer to this will come down to comfort level, funds available, and strategy you are looking to implement.