It took literally just ten minutes to map the whole block - building outlines, numbers and addresses, car parks, POI for the pub on the corner. The iD editor is ridiculously good, and mapping really is quite fun!
To contribute to OpenStreetMap, you only have to know somewhere. It's quite likely that almost everyone knows something that isn't in OSM.
Even 2 people from the same town, but live 1km apart could probably contribute different things to OSM.
Combine that with everyone wanting to see their own town/city/house/area on a map, and it's a recipe for explosive growth.
Most of my point still stands w.r.t. Firefox. QA, graphic design, education, translation and documentation are still skills that lots of people don't have.
As for knowing how to tag things, most of the time it is self-explanatory, and then you pick things up over time by looking at the wiki. I wouldn't worry about getting everything perfect from the start, for instance, you can add building outlines, and then in the future go back and add addresses if you choose.
http://labs.strava.com/heatmap/
So, depending on where you live, you may find local trails are on there (although you've still got to go in person to confirm they do actually exist, and to know exactly what they are - mountain bike trails, or narrow footpaths, or wide tracks for horses and 4x4s). In theory, it means you can shift effort away from sorting out gpx tracks, and more into getting the contextual information correct.
Pushpin is my favorite for iOS right now, because you can just mark the location and while moving on you can select what type of POI it is. It's also all in your edit history so at home you can for example then look up the restaurant and add more information in the browser. http://pushpinosm.org/
(As for me, I prefer jOSM - more complex, Java-based, not in-browser; more powerful in various ways: https://josm.openstreetmap.de/wiki/Download )
Intuitively I would have assumed that this would be really difficult to do, but the tools OSM provides for editing are actually quite easy to use even for people with no clue like myself.
You don't even require accurate GPS hardware or anything. Knowledge of your surroundings combined with the (blurry, but available none the less) satellite imagery might already be enough for you to really do good.
In my case, I've added building numbers of my neighborhood, marked one-way roads, added a few gravel foot paths where they were missing and I knew where there because I walk on them on my commute and so on. All this required zero hardware nor actual knowledge in map making (also: The changes are still in unaltered, so I assume they weren't all bad).
Using a cheap GPS tracker and a bike I furthermore added a few small lakes and a small creek close to where I live. The GPS tracker was very helpful as the satellite imagery was (understandably) just showing forest, but biking around the lake a few times was really helpful in giving me the correct measurements.
All this was both a lot of fun and absolutely trivial to do. I highly recommend that you give this a shot on your end. I'm a person with zero experience in map making and yet I could easily contribute my part and I had an absolute blast doing it.
Also, if you are good with directions, this isn't limited to the places you live now - I've also added a lot of detail to the map around the place where I went to elementary school (yes. The environment has changed a bit, but that was a great opportunity to visit the place again).
Contributing to OSM is a very pleasant and fun experience.