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#11
I don't think the primary concern is Microsoft licensing rather than the potential loss of functionality due to activation problems, caused by repeatedly switching hardware bases using a retail product.
I think the solution is called "Windows to Go" (WTG): I believe it is a feature using Windows Enterprise or Windows Education editions, rather than Retail. These editions are effectively equivalent to Windows Professional. Since the WTG is designed to be portable and for use on a range of hardware, the configuration of device drivers and any updates are handled when the base computers and the WTG storage device are put together for the first time, and subsequently by the routine WUAU technologies.
It would be worth comparing rates for MSDN Subscriptions with Enterprise costs, or whether your situation would qualify as an Educational use.
If your basic portable unit is an SSD (or two SSDs in case of a failure or other loss) these could either be hooked up by USB or external SATA connections.
If you are looking for 2x high end base units at either end of your journeys and something you can use during your travelling, WTG solutions would only consume a single licence - the cost of the license in this case would be negligible compared to outlay on hardware.
I have to say that having your data and system files moving around with you sounds like a more risky strategy than having your data backed up via a secure cloud solution, and accessing it through a VPN, but that is just my opinion.