This will provide you experience, a story to tell, and the credibility needed for adding additional clients.I'm happy to discuss more.

Also, any guides, info, or direction would be awesome. 

What further analysis should I be honing in on and key factors/metrics/info that may be providing inaccurate numbers?

I use all of them:-Brokers-Platforms like LoopNet, Crexi (my favorite), and BiggerPockets Deal Finder-additionally, brokers often have access to off-market opportunitiesWhen dealing with brokers, I've found that you have to build a relationship in order to get a good deal flow.

If you want more info about his meetup DM me. 

It never hurts to have an additional set of eyes to look after your property.

Are there additional steps you take when screening applicants, or do you take fewer steps?

If you stick with the larger down payments, you’ll have more stability and less risk, especially if the market shifts, but it will slow down how quickly you can buy additional properties.

The cons as i see it include loosing the 2 of 5 year cap gain exception, typically not an ideal rental because the emphasis at purchase was buying a good home for your family and not a rental with optimal return (my ex-home consistently has the lowest cash flow for equity in my RE portfolio), not disconnected enough from the property causes addition angst on damage and may result in over improvement.  

Here are a few ideas to explore that might help you get closer to homeownership in San Diego without selling:Cash-Out Refinance:Refinancing one or both of your El Centro properties could free up additional cash for a down payment without selling.