Thanks @George Aitken!
As of right now, my goal is to buy something within the next year, most likely a multi-family which I would plan to owner-occupy for a few years until I can build up enough equity to rent both units and move on. I plan on doing that through hard work and by continuing to build my name out here in the Metrowest as an honest, awesome, trustworthy, well-informed Realtor®. Depending on how many people I can convince of that will depend what my first move is!
Seeing as I'm now in a pretty solid relationship with a pretty awesome girl, I'll of course have to run this all by her "haha". See, her sister and her husband just recently purchased their second two-family home and we often hear about the stress that they've been going through keeping up with those. (e.g. stretching their budget thin, always improving or fixing something, tenant stories, snow removal, etc. - all of which I believe will pay off in just a couple of short years so I personally think these are great problems to have.)
The other option, buying a single family that's overdue for upgrades, and slowly chip away at things to add some equity. If done right, we could live in it for a few years and eventually turn a profit. I've thought about 203k rehab loan for our first primary residence if we're going to buy a dump, but I've also heard they can take some time and be a headache. (I do, however, take that with a grain of salt).
Down the road, when I have some capital to play with (mine or someone else's), I'd like to get into flipping properties. I've become really interested in the general workings of a home (structure, plumbing/heating, electrical), and I consider myself to be pretty capable of doing certain repairs and upgrades on my own with the help of google. (I also have a ton of electrician friends and a few plumbers and construction guys if I need to exploit them!)
First things first: bang out some deals this spring/summer, stash away a few more bucks for a down payment, and continue learning as much as possible! Any suggestions or input is always welcome. Thanks!
Brad