I don't have a great feel for rental rates these days so can only offer insight on neighborhoods.

There are some good bars in the South End (including sports bar type places) and that's the area that's probably most like Lincoln Park. But, you're right, there isn't sort of the local tavern feel to that area. And, no shot of private parking.

I live near Harvard Square and it's great. Lots of restaurants, lots of bars of different types. Your price range may put you closer to Porter Square and there are good places to eat there (and other fun parts of Cambridge are close by). Harvard Sq and Porter Sq are generally safer than Central Square too. But, you won't have super-easy access to the interstates.

I would not recommend Alston/Brighton for your demo.

Boston can be a bit tough for a newcomer -- Chicago seems much friendlier to me. But, it's a great town; lots of young people; lots to do.

Feel free to PM if you narrow things down and want more specific advice.