The bad news is that I discovered the wireless Internet access in my classroom was not working. Which meant I was at a complete stand still until I got home that evening. So I went home and started it up again. It does need to go through Steps 1 and 2 every time you re-connect. However, it goes much faster than the initial time. It also will continue where it left off for Step 3. The bad news is that I was back to the same snail's pace for uploading. I did turn off the hibernation option for the laptop so that it could work all night long.
That brings us to this morning. I unhooked everything and packed up for school. The wireless internet was working again. And....I was able to upload the remaining 5000+ songs in about 3 hours. Hooray! I also started the process on my school computer which has a separate iTunes library, so I will be able to combine the two. When I opened up iTunes Match on the school computer, it appeared that I would need to pay the $25 again. I was a little nervous that I would be charged again, but it asked for my Apple ID and password and then gave me a message that I had already subscribed. Because there are a lot of duplicate songs between my two libraries, I expect adding the school computer will be much faster (especially considering the upload speed at school compared to my house).
I have now activated iTunes Match on my iPhone and iPad, plus my school desktop computer and my school laptop. This combined the two iTunes libraries I had. I'm really hoping this will make lesson planning easier since I can access any of my songs from any school device I am using. I'll try to update again after I've had a chance to try things out and see how they are working.
Oh...the reason there are fewer songs available in iTunes Match than in my original library is because some of the "songs" in my iTunes are really voice memos, which can't be uploaded to iCloud.