I strongly suggest you leave your data at the office and remote into your system from home. This eliminates the chance the thumb drive with your HIPAA protected ePHI gets lost and the data stolen by *whoever*.
GoToMyPC is a good service. If you are cost concious, you can use LogMeIn which has a no-strings attached free version.
I agree with Midlakes that remoting in is the safest way to work from home. But, the question was can it be done. It can be done and can be relatively safe especially if you are only moving one or two databases. It is easy to encrypt the databases on the thumb drive and, if in fact one were to go that route, then Iron Key is the way to go. See Tips and Tricks (I believe -- can't remember if I posted it there) for a review.
When I talk about the 100 times, I am referring to the 500 times users have spoken about their fears of syncing and nursing homes, etc.
So, if one were only going home a few times a month, then it's feasible.
If I were going to work from home, I would use Remote Desktop or LogMeIn.
I am probably in the minority here, but for me it's just easiest and quickest to do the work at work and the home at home. I was discussing with a colleague what was worse. Getting home at 8:30 PM to the spouse or getting home at 7:30 and then telsing him/her
you now have an hour of work to do.