@Joe Burns - glad to see you getting off to an early start.
One thing any ambitious young guy in Boston should absolutely look into is affordable housing. These are income-restricted units (people over a certain income cannot buy them), which typically sell for about a third the market price initially. So you get to pay very little per month, while living in a place 3X as nice as your expenses would suggest. Additionally, in Boston specifically (it is different in Somerville and Cambridge), when you want to move, you can "appreciate" the property by exactly 5% per year. This is not a hopeful asking price, but rather the exact price you will sell it for. Example: $600k property on open market, you buy it for $200k. You live there 5 years. After 5 years, you can appreciate it 25% (5% x 5yrs). So you list it for $250k. It was a $600k place 5 years ago, so people line up to buy it at that $250k max allowed sale price, which is still a fantastic deal. Do some quick math and calculate your guaranteed ROI if you put 5% down.
You get a cheap place, with guaranteed appreciation, and no risk - you can predict with perfect accuracy what it will sell for at any point in the future.
There are some drawbacks...
1) you can't ever use it as a rental, so it's best use for you is as a really cheap primary residence with guaranteed appreciation. This is not a way to buy an investment unit. It's a way to cut expenses and eventually build a lot of equity when you sell.
2) obviously anyone reading this thinks "too good to be true". Well, it is true, so a lot of people apply for the lotteries. You could apply to every unit for 5 years and there is no guarantee you'll ever get one. But if you do, you're in great shape.
Here is an example of 4 units available via lottery right now in a new development:
http://www.maloneyrealestate.com/allele-bra-afford...
You can see the income limits - 80% AMI means 80% of area median income. 100% AMI means 100% area median income. Different units have different restrictions, so at some point you'll be disqualified from 80% AMI units, but you may still qualify for the 100% units.
The site I linked to, Maloney Properties, handles most of the affordable housing units in Boston (maybe all of the new construction units, and at least some of the resales as well). Get on their email list.
Other towns also offer affordable housing programs - however, the median incomes in those towns will be lower than in Boston, so you disqualify yourself at a lower income amount. You might still be okay for most of them today, but maybe not in the future, so don't delay doing your homework! The other major thing to distinguish various towns' programs is their respective appreciation rules - while Boston's 5% per year is very generous and allows folks to build wealth quickly, other towns favor keeping the costs lower indefinitely, and will dictate a TBD cost of living adjustment when you sell. This will be less than 5% per year, maybe less than 1% per year, as their goal is to maintain the unit's affordability for the next owner. Newburyport also has a 5% rule. Somerville has a TBD COL adjustment. Do some research, and figure out which towns' rules favor a young guy trying to build wealth.
In Boston, Somerville, Cambridge, etc, you are typically going to be limited to 1 or 2 bedroom units. If you would be willing to go further out, there are often 3 bed units available. Now we're talking about buying a house that will be big enough to hold your future family, on expenses you can afford (by definition) when you're 20 years old. Talk about a game changer.
Here's a great resource for *all (sometimes the Boston proper ones don't make it on this list, but I think all others do) MA affordable housing properties.
Mass Access Housing Registry
Good luck!