You don't HAVE to buy points, but if you have a high DTI, the lender might not be able to do the deal unless you do, we can't tell from the information that you've provided here. 

Providing something unique in a very competitive environment is essential Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

Once you have that rolling and you understand the game you can then invest your W2 income into additional properties. 

-I like investing in college towns, as I feel it provides STR and LTR opportunities.

I REALLY WOULD LIKE TO DO IT BUT I'M ON THE FENCE, MY WIFE IS NOT TOO SURE, SHE THINK THAT'S A LOT OF MONEY, WHICH I ALSO UNDERSTAND THAT IT IS, I'VE HEARD A LOT OF TESTIMONIALS AND VERY POSITIVE, I'M CURRENTLY UNEMPLOYED AND KNOW THAT IF THIS PAN OUT WOULD BE A GAME CHANGER FOR MY FAMILY AND OUR FUTURE.

It sounds like your tax advisor should have included the depreciation from the cost segregation study provided by Capital Square.

I'm currently living in the DMV area (specifically, Germantown MD).I'm super new to the game, and am slightly overwhelmed with the amount of information there is! 

You'll find it's a whole different game than your rental property in a high cost state.

However, I would appreciate further clarification on what you mean by having a Plan B, C, and D.In my experience playing the BRRRR game on a smaller scale, typically with homes valued around $200,000, I have found that it can be challenging to generate significant monthly income, Instead, the focus is often on building a portfolio without having to make substantial out-of-pocket investments, which is indeed advantageous.

If new communities were being built on the outskirts of cities and that trend continued, as cities grew new parks would provide for parks to (I know this can be a bad word) be gentrified without losing the affordable housing.