Long-term I'd hope to grow a buy-and-hold portfolio, but I'm very focused on this first purchase for right now.Since I work downtown, don't own a car (and don't want to), and spend most of my time in Central LA, I'm looking really closely at areas around downtown: lower-cost areas with decently affordable 2-4 unit buildings (in the $400,000 to $800,000 range) like Pico-Union, areas around USC, and even up around Hollywood/Koreatown when the rare good deal shows up there.I've been looking around on Redfin a bunch, but have seen little to nothing that satisfies Josh and Brandon's "Two Percent Rule" (or even 1% rule).

Not to mention the taxes on condos are much lower than single-family homes especially in the Chicago area where I am at.

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.