I booted Linux Mint from a USB drive to see whether I could eventually move away from Windows. The basics look good so far: Firefox and LibreOffice cover much of what I need, and I expect there are suitable Linux applications for media and image viewing.
The bigger question is compatibility with software I already use. I have several custom programs I wrote in Delphi 3, some older format-specific readers, and Delphi 3 itself. I also do a small amount of installer development with Inno Setup. Games such as Deus Ex are another consideration.
Can I install Wine and these Windows applications into the live USB session to test them? If so, will the results be meaningful, or would I need a persistent live system, a full installation on another drive, or a virtual machine?
4 Answers
The only dependable answer is to test each application. Wine compatibility varies with the program, its installers, required libraries, graphics drivers, and copy-protection systems. Older Delphi applications may work, but Delphi 3 itself and Inno Setup could require extra configuration or may be easier to run in Windows.
For Delphi 3, Inno Setup, and any other Windows-only development tools, a Windows virtual machine is probably the most predictable solution. You could also dual-boot while transitioning. For games such as Deus Ex, Wine or a compatibility tool may work well, but test with the graphics drivers you intend to use rather than relying only on a live session.
A standard live session can let you install Wine and try applications, but most changes are stored only in RAM and disappear when you reboot. Storage and memory limits can also make the test less useful, especially for larger programs or several compatibility environments.
If the USB was created with persistence, installed packages and configuration can survive reboots. Another option is installing Mint fully onto an external drive. That gives you a more realistic environment for testing, although ordinary flash drives are not ideal for constant writing, so use a reasonably fast, reliable drive and keep backups.

That makes sense. I was hoping there was a way to get a useful compatibility check before committing to a full installation.