OpenStreetMap does not store photos. There are other services for that, they build upon OSM and even recognize features such as street signs in photos so they can be easily added to the map.
Regarding ease of contribution... I knew exactly nothing about mapping a few months ago. I saw the recent OSM birthday news and decided I should start contributing. Someone here on HN recommended Street Complete so I just downloaded that. It was really easy to contribute data using that app, it asks you stuff and you just add the missing information or confirm that it's correct. Added lots of local information for my city and neghborhood.
Eventually I noticed some roads were wrong and downloaded Vespucci to fix them. Turned out to be surprisingly easy once I learned about ways. Just pick up a few dots and move them, maybe add some new dots. Then I figured I should probably add my house to the map. Then why not add my neighbors as well? Wait, I'm using the satellite imagery as a reference to trace the buildings. Are the streets even aligned with the images to begin with? I figure I should get some GPS traces to verify. Wow, I always thought GPS and its 3 meter precision were impressive but it's actually not good enough for this purpose. Looks like I can set up a differential GPS system with a base station at a precisely known position, what a cool project. Expensive though. Oh look, new Android phones provide access to raw GPS pseudoranges which is just what I need to differentiate GPS fixes. They even have L5 GPS, sweet. I should try making an app for that when my new phone arrives. Maybe I can repurpose my old one into a GPS base station so I can compute GPS traces with centimeter precision. Meanwhile, I'll just average the results with JOSM. Man, JOSM is such a nice editor. Free software, works on Linux. I should learn all of its features.