weil Site this is possible to some extend. I’m running Windows 10 with eclipse for C/C++/Assembly
I’m using a cross compile toolchain tu directly compile on the windows machine. Than you are free how to transfer to your Pi.
When Linux is running on it you may choose ssh and can also configure eclipse to remotely debug on the pi.
When doing bare metal you may put your kernel onto an as card or build or reuse a small boot loader on the pi to transfer the new code using the serial UART interface. Depends on how experienced you are and what you want to achieve
Debugging in bare metal is rather hard. It’s more of an “intelligent” placement of output written to the UART console which allows you to get a glimpse where an error may be located...