OSM2Go uses projects to organize the work. This happens for mainly two reasons:
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The world is too large to be handled by a handheld device, so the concept of projects breaks the world down into little pieces a user is working on.
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A handheld device is likely not always online. Thus changes are done locally, stored in the project and uploaded/synched at a later time.
A project consists of several parts:
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The project file itself containing the projects name, the geographic area it refers to and information required to up- and download data.
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The osm file being the information downloaded from the OpenStreetMap servers and containing a snapshot of the state of geographic area specified in the project file at the time of download. The osm file is never touched by osm2go unless it is overwritten by a newer version.
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A diff file containing the changes the user has made to the data in the osm file and which has not yet been uploaded to the osm server.
The upload is a delicate step as this actually alters the OpenStreetMap main database. This also is the only step that alters it, so unless you perform an update you can play around with the map as you want without risking to destroy anything.
So you actually have decided to perform an upload. You've changed some ways or nodes. These changes are currently in the project diff file and you may actually leave and restart osm2go without losing those changes. Selecting upload from the menu will first give you a raw overview of what will happen. You'll be told how many way and nodes you've changed, how many have been deleted and how many have been created newly. Please take a short look at the numbers presented. Do they make sense? Do they e.g. indicate that something is to be deleted, but you didn't delete anything? Please don't go ahead then, but try to figure out what happened.
If everything looks reasonable, then enter your OpenStreetMap account data into the username and password fields and click ok. A new window will open containing a text buffer. This is the upload log. It will record basic information about your upload and may be especially useful if something goes wrong. Let's hope you entered your username and the password correctly. Then the upload should succeed. This usually only takes a few seconds. If your upload went fine and you actually changed data on the servers database, osm2go will then re-download the entire project area from the server. It will free the map and redraw it on basis of the newly downloaded data which now hopefully includes the changes you just uploaded. You should see the same map as before, but this time it comes entirely from data stored on the main server. Congratulations, you just contributed to the OpenStreetMap project!
You can go ahead and continue editing and uploading. OSM2Go will take care of your changes and make sure everything is stored until you upload it to the server so the server takes over the maintenance of your contributions.
Getting started with osm2go is not dangerous since osm2go works offline most of the time and does not touch any data stored in the OpenStreetMap database unless being asked to do so.
In addition to the item presets shipped with OSM2go, which are in turned derived from the JOSM ones, a user can add local presets. These presets must be stored in the directory ~/.local/share/osm2go/presets. For a ZIP file named foo.zip a new directory "foo" should be created inside the presets directory. Within that directory the ZIP file should be extracted. OSM2go will automatically detect the new presets on next startup and add them below the builtin presets in the presets picker.