I received a bachelors degree from Mercyhurst University and have wrestled from pre-school all the way through college. 

We both also have finance degrees and are savvy with finances and from an income perspective we are inline with each otherSimilar to what JD stated - We have a living trust where everything eventually goes to the kids and if something were to ever happen we would sit down like adults and resolve it without being vindictive. 

Did you go to School and get a Degree that gave you a JOB?

My goal is to find a cash-flow-positive rental property that I can manage while finishing my degree, setting the foundation for a real estate portfolio I plan to grow steadily over time.

Bam, now I can in fact somewhat speak "in general," and I can say that with a fair degree of confidence BECAUSE I've zoomed into that one thing.

I think we all do to a degree.

Your disposition may be to move forward with that as i believe i read in your introduction - but not needed to understand and develop some degree of comfortability.  

I takes a substantial degree of work and ability.

Keep in mind, no matter how many round trips you do with entitlements you will always face some degree of adversity because there are so many variables, many of which are unknown until you start your process.

I have dual graduate degrees in both economics and finance.