Am I missing something or do I fundamentally lack an understanding of how this works?

Before you consider spending money to invest, make sure you have the personal fundamentals covered.Our first rental was a duplex.

I think that I have to gain the skills of 1. fundamental analysis (reading financial statements or proformas) 2. deal analysis, and 3. structuring the deal correctly.

This is production.When you buy personal housing, you're helping your own situation and you might benefit from appreciation, but this is fundamentally an act of consumption, not production. 

Taking calculated risks are one thing - getting too creative and putting your kids meals in jeopardy is another.Stick to fundamentals. 

Stick to the fundamentals. 

The last quarter (annualized) is 6.7%.The fundamentals and economics are strong for Orange County, however, from an investment perspective (and what we advise our clients), your investment capital can go much further in other markets that have similar or better appreciation potential, while being able to generate positive cash-flow while owning more properties with less land-value risk (depreciation).With a median sales price of $585,000 and median SFD rent of $2,350, the rent-to-value ratio is a mere 0.4% -- far below our minimum target of 1.0%.Thanks Karen.Continued success!

I think those fundamentals will help really carve out the emerging market of private investment back into mortgages in general.

I'm looking for a Real Estate mentor in Maryland( PG county preferred) who can coach me face to face on wholesaling, rehabbing, and all the fundamentals to getting started.

Fundamentally, that is not unreasonable.If they are not willing to do that, then I personally would not do the deal.