I ended up using STLINK V2 for development rather than bootloader. It's very reliable, fast, and allows to debug with break point, examining registers and peripherals and single stepping. Will address later how it can be updated in the field without an STLINK V2, maybe using the built in DFU bootloader? (I haven't research it yet).
As for development environment, I am not using VSCode + PlatformIO using the arduino framework and it works very well for me.
Having problem to make HID bootloaded 2.2
Bootloader for STM32F103 and STM32F4xx micro-controllers
No special driver is required. Support for Windows, Linux and Mac Operating System
No special driver is required. Support for Windows, Linux and Mac Operating System
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