Conclusion
This is not a review of a specific product and instead as far down the opposite lane of a review as we go here on TechPowerUp. I have personally used every covered product (or combination, as in the case of the Kingston KC2000 + Silverstone MS11) for a separate work trip each, and have become intimately familiar with the pros and cons of each option. There are the obvious effects of going from a USB thumb drive to a USB external drive in terms of available capacity and ease of transportation, with the former ending up being my go-to for conference talks and meetings alike and the latter used for more data storage. Encryption was most definitely used in all available cases, as it was also downright mandatory where the host organization/country had stricter laws when it came to potential IPs generated while on the premises.
It was thus a personal interest of mine to see what the various options available were, and the ease of use as a bog-standard data storage drive as well as the various encryption options offered by the device/manufacturers. A software-based password generator was the minimum in my case, and no doubt many others are in a similar situation, but such password generators are not unique to any particular device, and there are several 3rd-party solutions. An onboard keypad keeps things simple, as with the Kingston DataTraveler DT2000, which does mean the drive ends up being bulkier than others. SecureData went with licensed ClevX patents and their own manufacturing to offer high-end Bluetooth-based encryption for their new SecureUSB BT and SecureDrive BT series, which worked very well with 2FA and mobile unlocking options as needed, but does mean that you absolutely need a compatible mobile device with you at all times. The options that worked also offered managed solutions, and the SecureData implementations especially allow for extensive, certified, and easy to use admin and user controls as discussed before. You definitely pay for it, especially with an annual license in the latter case for the management options, but they are optional and for those who need them.
It was perhaps fitting then that the outlier, which unfortunately did not work out well, was also the combination of two products people usually do not associate with this specific scenario of portable storage and encryption. When it comes to pure performance and a good balance of size, cost, and storage, the Kingston KC2000 M.2 SSD paired with an external USB enclosure, such as the Silverstone MS11, does offer a lot, especially since you can actually downgrade to a slower SSD and a USB 3.1 Gen 1 adapter if you only have slower USB ports available. But using a drive where it was not intended and comparing it to products engineered for that one purpose meant that very thing worked about as well as I should have expected, I suppose. There may well be a way to get the certified security features working, but for now this article hopefully helps those in a similar situation to the one I found myself in, however niche it may be.