Pfd,
You'll be able to get a job soon after school, but it'll most likely be at a regional airline. That means you'll have to move. Even if you can live on regional pay where you are (doable in most regional cities), you might not want to. You'll be looking at a minimum of 35-40 flights for your shift, if not more than that; depending on the shift and the shop, you could easily do 50-60 or more flights during a shift! They're not evenly spaced out, either; it's not like you get 4, 5, or 6 flights per hour for 10 hours. The flights will come in bunches, meaning you may have to do 10-15 in an hour. Then there's the matter of always doing the same flights day after day, week after week, year after year. Would you want to be a regional lifer?
Even if you don't make one of the mainline carriers; if you don't make the Big Four; don't despair. There are cargo airlines out there, and I'm not just talking about FedEx & UPS, either. You have Kalitta in MI, Western Global and Amerijet in FL, and so on. Kalitta pays pretty decently; though not tops in the industry, the cost of living is a lot lower in MI, so your salary will go farther in Ypsilanti than it will in a major airline's city. After a stint at Kalitta or WG, you could maybe get in to FedEx or UPS since you'll have cargo experience. There are also the ULCCs, the ultra low cost carriers such as JetBlue, Allegiant, or Frontier.
Yes, you'll be able to get a job after school, but it'll probably be at a regional, which means you'll likely have to move to take the job. Then count on spending at least 2-3 years to build experience. Though you might not make it to a major with just 2-3 years, going to a cargo carrier or ULCC would certainly be in the cards, and you can have a rewarding career there.
If you want to commute, it should be easier for you since you live by BOS; it's a larger airport, so direct flights should be an option. If you want to commute, try to avoid connections at all costs! The more connections you make, the more chance there is of getting bumped off your flight. Even if you have no problem making it out on the first flight, you could very well get bumped in the connecting city; that happened to me once. Though I made it back with plenty of time, I spent an afternoon finishing a John Grisham novel @ DTW! If you can do a direct flight, that's a lot better for commuting; once you're on, you should be ok. As a nonrev, you'll fly standby, which means you'll be among the last to board. Anyway, you could take a crash pad in your regional city, then fly back to BOS on your days off. One of my trainers commuted, and he made it work...
As for me, I tried out commuting, and I didn't like it. The closest airport to my house isn't a large airport; that meant a connecting flight, and connections are always a PITA! You're near BOS, so I'd think that some direct flights will be available to you. Direct flights would make a commute easier. I was going to rent a crash pad where my regional was. The landlord was a AA pilot based out of NYC. He commuted. He made it work because he was able to get direct flights to and from NYC. I'd only commute if there were direct flights between my base and my house.
Those are my rambling thoughts. I hope they help, and good luck!