Figuring out what our ideal life to maximize happiness was HUGE.

I'm going to venture a guess that your CPA doesn't do a whole lot of returns with rental property on them.The ideal scenario is to have positive cash flow, but a tax loss, but that's not always best for every person, particularly those who don't want higher leverage on their rental properties.Generally, a property that is owned outright or is in the last third of it's mortgage life will show pretty strong profits, even after depreciation.  

Ideally, my goals to get started are long term holds with positive monthly cash-flow.

Mortgage lending still looks solid to me ... if you want to see unsound lending practices that are about to run aground, look into auto loans:http://www.valuewalk.com/2017/04/auto-subprime-loa...

Ideally we would have started with a duplex or triplex, but we did not know about real estate investing until recently and now we have two young kids and do not want to deal with tenants right next to us.

Ideally, we intend to have as much profits go back into the business for new investments as possible, but at some point we hope to quit our day jobs and start generating our income from our investments.

A lot of people think they would need to pay this out of pocket first like with auto insurance, not the case. 

How do I deal with this issue?  

Ideally, someone who's worked across all jurisdictions in the DMV.

However, having issues with auto use as it is across the street from residential.