Ross Ellington , if the sum of your mortgage interest, any points, and property taxes exceed $6,300 for single filer or $12,600 married filing joint or $9,300 for head of household THEN you would elect to itemize your deductions and lower your taxable income by the sum of interest, points and tax.

Basically, I want to get to the point where I can start earning at a level where I can move out of my parents house, pay down my loans (hopefully before my own [future] kids are racking up their own), and perhaps even retire... ...all before I die.

I can lower my student loan payment because I'm paid ahead quite a bit. 

. $250k should be able to get you 4-6 SFH's in a good city, lower B class housing which would cash-flow well, each with 25% down. 

It's a beautiful city with good quality of life, and prices are much lower than the DC area. 

I joined because I am looking to expand my knowledge and network in the world of property investing in order to take it to the next level.

ONLY look where the best schools  are, in the best neighborhoods you can afford.The neighborhood and  house should have instant curb appeal, sit 'at or above' street level, yard for the kids to play in.

Then I would be only borrowing 42k and then paying the mortgage which would probably be a lower payment than the HML. 

Samuel,In my mind it boils down to the level of service that you expect from whoever you bring in.

(We went into contract at a price lower than their original asking price and their argument was they thought because we were purchasing it so low they I wasn't getting a commission?