Forget the North End, it would be ridiculous to have a car there and most of the time it's discouraged any way. Most of the neighborhoods in the City of Boston have resident parking where it's a valuable commodity having a parking spot these days, NOW more than ever before in the City. If you DO end up finding a condo/apartment in the City of Boston make sure you go to this site to update yourself on the resident parking forms/renewals & all that right here:
How to obtain a Resident Parking Permit - City of Boston
I know Cambridge always had problems too, but there's pockets of Cambridge that don't have trouble that way. So it depends on where your condo/apartment is located. With Jamaica Plain, if you find something there it might be better than other parts of the City, but again you'd have to actually see the apartment/condo for yourself to see what each particular situation is with it for parking. Brookline would be really good yet it always had issues with parking from what my relatives have told me about living there, but than again, you might luck out and get off street parking there too you never know so it depends on each individual situation & what you find. You're going to have to do your homework on it here when you get the chance.
I'll tell you if you're a jogger, or if you run or even like to walk a lot, South Boston's "East Side" is where you'd really enjoy living I bet. They have two MBTA buses going thru that neighborhood all the time to get you to either South Station for the Financial District OR over to the Back Bay area of town. You'd only be a mile away from work. They have City Point Beach to jog, run or walk along right within walking distance to a condo/apartment. So think about looking in that neighborhood too where it's so ideal. Great restaurants, bistro's & pubs along East & West Broadway too. You'd really like this location to get in to downtown Boston. There's quite a lot of people living there in your age group now more and more. I lived there myself for over 15 years and loved it during those years, it was ideal!
Well like I said now they have "Resident Parking" there with signs on every street, so definitely read that website above to get yourself familiarized with how it works in the City. I lucked out living there back then because I used to park in back of a store and it was cheap to keep the car there & they even plowed me out in the winter time! BUT those days are over unfortunately, so forget about that happening these days! They're all wise to it all now & want their big $$$.
Don't forget the city of Somerville is good too you know, with the MBTA bus running right thru it all the time. Remember Davis Square, it's quite the place these days; especially good for restaurants, pubs & bistro's & for jazz lovers, bike riding etc...you can read about it here:
Davis Square - Wikipedia, the free encyclopedia
Good luck wherever you decide to live! You're going to enjoy living in one of Boston's neighborhoods a lot OR even in the City of Somerville or Cambridge would be ideal for you!
