DaveL
2
The answers to 1,2 and 4 are closely related.
Your uploaded tracks will appear as a series of points. It is up to you (and every other mapper) to create a series of lines on top of those dots to represent a roadway with one of a selection of editors. Joining those lines together, and adding properties (such as road names) completes the interpretation of the GPS track to a road on the OSM map. Provided you have enough GPS data (and trust in that data!) to make the lines, there should be no need to gather multiple tracks for the same road.
I think question 3 sounds a bit more personal. There is obviously a compromise to be made between the frequency of track points you allow your device to collect and the storage capacity of that device. See what works best for you.
eg My device can store 10,000 points. In the car, I typically let it record at one point per second to give something approaching 3 hours of data. When travelling much slower (on the pushbike), the device records at one point every 3 seconds, so I can wait longer before transfering data to the PC. I am sure every mapper has their own ideas about all that.