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Thanks CA3LE, I'll look into that after the summit. Just curious - any chance you run Dropbox? I keep 99% of everything in Dropbox so backing up really shouldn't be too bad but if I have to reload any programs that aren't Windows, re-syncing this program could take a while and I'll have to factor that in... However, Sean is a genius. I can't believe I didn't try my mobile upload speeds! Turns out...that's not doing to hot either! Only 688 kbps, whereas my host average shows up as 23.9 Mbps. The city average is only 2.5 Mbps, which is still way better than what I'm getting, but is "host" the internet provider that I'm connected to? I'm feeling like I'm back at square one BUT slightly relieved that maybe it's not my laptop afterall? GAH, thank you guys so much for your patience and all your ideas!

Just to rule out the laptop completely, try running a speed test on your mobile connected on the same Wi-Fi connection. In your phone's web browser, go to testmy.net, then run the upload test. If the upload speed is much better on the phone, then the issue is likely a software issue on the computer (especially if you tested by both Ethernet and Wi-Fi). If the upload speed on the mobile is also poor, the issue is with the home's Internet (try again with the laptop switched off to be sure). In this case, if your mobile has good 4G reception there and you have a large data allowance (e.g. 5GB or more), try running an upload test over its data connection from your laptop. Most phones have a hotspot feature (On Android it's Settings -> More -> Tethering & portable hotspot). Turn this on and connect your laptop to that Wi-Fi (check phone's screen for its Wi-Fi password). Then run an upload test. Turn off the hotspot feature afterwards or reconnect your laptop back to the home's Wi-Fi network.