Cash flow seems like the obvious one but I'm struggling with the concept of building equity at expense of cash flow. 

Or put in your interest rate here, and your loan balance there.The art is where I think most people struggle, and I don't think this can really be done without real world knowledge.  

From what I read and understand, this means I'm likely going to struggle with getting a loan, not even considering the inability to pay any down payment.On the other hand, my parents have significant liquid assets, (think on the order of > 500k), that they are potentially looking to diversify into real estate.

They are very different, which is making me struggle with comparing them.

Airbnb without a pool or waterfront prop is going to struggle anywhere in Florida

However, I still struggle to understand the art of estimating rehab costs. 

I work in wholesale in Indianapolis and still struggled to find deals that would even be close.

I think this would be really insightful to other rookies who maybe have a fear of failing or are struggling right now.

It's heavily dependent on the types of properties and the effectiveness your processes and systems.If you don't have systems and processes in place, you may struggle to manage 30 on your own.

I have heard of a fair number of college students, particularly freshman who struggle to adjust to college and have to return home for mental health reasons.