OK! Looks good 
I hope it works like you want it to! 
Thanks! It did work well for a while - the details below:
So I got the internet connection set up and running on 2/4, uploading to Weather Underground at the ID of KNJLONGB3. Uploads continued flawlessly until stopping during the morning of 2/18.
I managed to get on-site on 2/20, and discovered that the DataJack apparatus was in hibernation mode. DataJack tech support (which is very helpful, by the way) wasn't sure why the unit had started hibernating on its own, and we came to the conclusion that there was probably a power failure involved. I got it working again while I was on-site on 2/20.
Uploads to WU then continued flawlessly again, until 3/3. This time, it appeared a thunderstorm had struck and that the power had probably failed on-site - the last observation uploaded to WU included a 38 mph wind gust and 0.30" of rain in 10 minutes. This was odd, because my station recorded wind gusts up to 47 mph on 2/25 and there were no power issues.
I got back down there again on Friday, 3/9. What I found was strange: the laptop was running and the DataJack was running (and still connected to the internet), so even if there had been a power failure, it hadn't lasted long enough to drain the batteries of my units. Still, I bought and installed a battery backup for future peace of mind.
But when I opened the laptop, I saw a message from Windows displayed that indicated "low virtual memory" on the computer. I don't know much about this, and have seen the message before on the laptop (and thought little of it). But Cumulus was open, and not running - it was frozen in time from 3/3.
I concluded that Cumulus had probably drained my memory, so I closed everything down and started it up again, this time also running VirtualVP and WxSolution alongside Cumulus. I assigned WxSolution to upload to PWSWeather, in case Cumulus had issues again.
Yesterday at 5:10 pm, uploads to both WU and PWS stopped. I'm almost positive this is due to the same "low virtual memory" issue as before. The laptop is quite old - from roughly 2004 or 2005 - and struggles.
The solution? I'm getting a netbook! A newer, stronger system should be able to handle these programs without a problem. The remote setup should be back in action within a couple weeks.
As a side note: I checked my virtual memory usage here at my home weather computer, and found the results to be very telling: Cumulus uses 67.2 MB of virtual memory, while VirtualVP, WeatherLink, and WxSolution use only 16.7 MB combined. So, on an old, weak laptop like the one I have at the beach, it's conceivable that Cumulus could have swamped my available memory and caused the laptop to stop working.