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1) Yes. KitProg can't support SPI bridge, but KitProg2 can. See the driver list:
2) You can find KitProg2 driver's hex in some kits' install files, such as:
Recommend to double-check if their hardware are compatible before the 'upgrade'.
Then you can program your KitProg with KitProg2 driver's hex through SWD interface(I guess an external debugger, for example MiniProg3 is required) and make it become KitProg2.
3) Of course, you can buy a CY8CKIT-145(KitProg2), CY8CKIT-149(KitProg2) or CY3295(TrueTouch Bridge). They can support SPI bridge.
Thanks for the information. I have a few PSoC 5LP kits lying around. Maybe I'll see what happens if I "upgrade" the firmware from one of the KitProg2 kits you listed. If that doesn't work then I'll buy one of those kits just so I have some SPI debugging functionality.
Again, thanks for the info.