Your connection issues are interesting, mainly because they are bizarre and your comment "It's interesting because the same variety of devices and networks worked perfectly fine this summer" So your students are using the emulator OK?
The Dell Win to AI Companion is very standard.
A Chromebook to AI Companion? I did not know that was possible, possibly using the LINUX drivers?
Several virus checkers have issues with AI2 connections, notably preventing the emulator from running. I know AVG has a setting called a link setting that when adjusted permits AI2 to communicate.
Is it possible that your IT department made changes to the firewall this summer? Port 8004 must be accessible. Your entire scenario appears firewall related. Another possible issue is the number of users in your class. You network might be too slow to permit many users of AI; I do know that when some schools have slow network connections, that students early logging in have few if any issues, however those logging in later have serious connection problems. Could this be an issue.
What is strange is that you also have issues at "home." ... What kind of Internet connection do you have at home? DSL, dial up or are you attempting to use a 3G network hub (which usually work poorly)?
Building a app 'blind' in AI2 is possible and can be done as you describe; by building an apk then loading it to a device. It certainly works but is awkward at times and it is generally significantly easier to build using the live development options.
Of note is that Nexus 7 is one of the platforms MIT uses for testing, however their primary computer is a Mac.
Are you using the Windows setup for your Dell? Are you using the Linux setup for your Chromebook?
Here is some of the standard stuff to read regarding connection issues:
Another thing that prevents AICompanion connections that might be installed on your PCS:
If you have BlueStacks on your home PC (BlueStacks is a special emulator that allows Android apps to run on a PC). The Google emulator on AI2 cannot run unless BlueStacks is disabled and all of the BlueStacks processes are shut down. On a Windows PC, you use the Task Manager to 'kill' running processes.
Make sure your browser is one of the supported browsers and up to date. AI will not work with Internet Explorer, but works fine with Safari, Firefox and Chrome...perhaps this is the issue?
Try reading those, perhaps you will find something new to try. Let us know what you find. Having to build all the time blind and build an apk works but perhaps we can find a way for your students and you to have more fun.
In plain words, you are having no luck with live development. Is that the case? Does your emulator work?
Regards,
Steve