Seinfeld episode with George fighting over a parking space. Unfortunately, if George was living in our wonderfully modern world and not practically the stone age, he would be able to use technology to secure his perfect parking space. Luckily, you have the benefit of doing so!
The first glorious service we want to introduce you to is PrimoSpot. Using Google Maps, Primospot plots parking signs street by street and explains all their ridiculous rules. As of now, PrimoSpot is unable to tell you if the spot is open but they say they are working on a solution which would certainly drastically increase the usability of the site. But that's not all it does. It also categorizes garages and bike racks for the cyclists out there. They also have a companion app which the New York Times has written about. Because the website requires human input to create the maps, it isn't yet available for every area but they are working on adding more cities as quickly as they can. And they've done a good job at making sure the major cities have been covered.
If you're looking for an excellently designed and free app that helps you after you've found a parking spot, Parking Mate is it. Never receive a ticket again because you can quickly input your parking time, rules, street cleaning dates, or any other irregularities with the meter time and be done with it. Free up your mind to think of other things while you're phone does the work to remind you before your meter expires or if you need to move your car for street cleaning. You can even take photos or save a GPS marker to remember your location. But taking the photos is extra helpful if you're up against parking authority personnel. Photographic proof is hard to argue against so if you get a ticket even though there is still time in the meter, use the app to take photos proving your position and time. (Image: Flickr member Baptiste Pons licensed for use under Creative Commons.)