Trying to find easy, cheap parking around Boston is like searching for the Holy Grail, except harder and without the considerable on-screen chemistry between Alison Doody and Harrison Ford. Until now, with PrimoSpot.
Just expanded to cover Boston and a few select 'burbs, PS is a simple (and free) site that shows where on the street to park your car -- or bike if you're livin' green -- as well as aggregates hourly, daily, and monthly rates at hundreds of parking garages across town, so you can confidently know you're being taken for a ride, even before you actually take that ride. To avoid the meter maid's wrath, type in the address/intersection/zip code where you're motoring, and your ETA, and the site will generate a Gmap littered with icons representing nearby parking meters, bike racks, or garages; simply click on the marker to reveal all the relevant deets like address, hours, rates, type of street parking, and how long you can park there, as well as check out pics of the actual meter, street sign, or bike rack, (check out the luscious rack on Kendall Square!). Because garage prices usually leave you feeling dirty, there's also a sortable, real-time price chart that regenerates as you scroll around the map and provides pertinent garage info like number of spaces/size availability/proximity to Tomorrowland.
PS has a feature to help you remember where you left your wheels and also offers iPhone and Google Android apps to find parking en route -- further reducing the odds of having a withered old man point out that you "chose poorly".