Yes. I do similar, and it's still working this year.
I recently switched to using snapshots of a better-maintained Windows install with multiple softwares, instead of previously one or two barebones installed programs per VM.
Aside from enjoying going through these motions as a hobby, (which is totally fine), is there actually any reason to do this? There are so many ways and attack vectors through which your credit and tax info can be stolen that it just doesn't seem worth the effort.
Imagine airgapping TurboTax to submit your return and then an IRS employee sells your data
The big difference is that the IRS employee selling your data is illegal. So sure, your info can still end up out there in less-legible circles, and some drive by randos can play around with it or perhaps if it's widespread enough your acquaintances could look you up, but the main advanced persistent threat - the surveillance industry - can't really use it. Whereas when you use surveillance based software, since we lack meaningful US privacy legislation, you're assenting to "terms" that allow the surveillance industry to use it for whatever attacks they can implement - eg real time price discrimination, insurance rates, surveillance based authentication, etc.
Vestigial hobby. I used to do lots of privacy&security exercises, partly on-principle, and partly because it seemed like a civic responsibility as techie-citizen.
Pragmatically, I'd still rather not give that data more widely than I have to.
I see. I used turbotax this year and it didn't require an internet connection except for: installing the latest updates and the actual e-file obviously. All the calculations for credits, deductions, and maximizing your personal tax situation were done locally. What you're describing could probably work.
