First of all, welcome to AVS. You should find a lot of useful information and help here. A couple of things you might want to do. First of all, add your location to your profile (see mine at left). So much of this is location-specific, it helps to know where you are.
Next, check your local thread. In your case, it would probably be Boston:
http://www.avsforum.com/avs-vb/showt...57#post9445957 Nobody better to give you advice than those familiar with your local stations, terrain, etc.
You'll also find the
OTA FAQ to be rather useful in helping you navigate through the sometimes confusing world of OTA reception.
That said, I'll tell you that a roof-mounted antenna is almost always going to be the best answer. You're just over 20 miles from all of Boston's transmitters and they're all roughly in the same direction and all of the digital stations appear to be UHF (for now). If you don't want to go the roof route, you may be able to get by with something along the lines of Zenith's
Silver Sensor antenna or a
UHF-only solution . I always give the same advice: Start cheap and keep receipts. Sometimes, a $5 set of rabbit ears will do the trick. Given the obstructions you mention, however, I'd bet you're going to have to go higher and/or larger.
Doc