Look at the downside. Even the phones on planes tend to use ground towers because of cost.
Actually, most of the phones on planes use Satellites, since, well, there's no ground stations when you're flying over the ocean
It could get ugly legally, but with a decent lawyer you should be able to prove the logical separation, and let whomever needs it take the copy of the VM and do whatever they want with it while keeping your personal stuff intact and private. I wouldn't be surprised if this starts to become the norm in the tech industry, as it solves lots of problems for employees who frequently cross the work/home/life balance.
Note that I primarily work from home, which makes things a bit simpler.
... or Expedition 18?
I don't agree with the Massachusetts decision to attempt to stifle the presentation. This was foolish on a number of levels, not the least of which was it will probably help draw far more attention to the hack than it otherwise would have obtained.
That being said, it is perfectly reasonable to not "fix" a system if the cost of the fix is more than the cost of fare evasion. Look - in many cities "evading the fare" is as simple as getting on the bus and choosing not to pay. These systems depend on users for the most part obeying an honor system with periodic random enforcement by transit personnel checking for passes / ticket validation. This is done across Europe and in a number of cities in Canada (not sure about the USA). Why do this? For starters most people aren't jerks, and pay their fares. Second, there will ALWAYS be a way to evade a fare system without massive (expensive) enforcement that would cost far more than the added fare revenue. You would not get on one of the systems where there is no ticket check on entry and then crow about how you evaded the system (or you wouldn't without looking like a complete dork).
It's worth noting that this injunction is not analogous to software companies hiding known exploits in their systems where their customers may suffer the consequences. Boston IS the end user.
Moving people from place to place should always be the highest priority of transit authorities. In general most people are good about paying their fares. Dealing with smalltime one-off thieves is a waste of their resources.
If you use the system without paying, you are a thief and you are doing a tremendous disservice to your fellow citizens.
There is one way to find out if a man is honest -- ask him. If he says "Yes" you know he is crooked. -- Groucho Marx