Following a recent discussion with a user Vector35/binaryninja-api#5833, I learned that the LLDB 18.1 actually supports Windows remote debugging (from macOS/Linux). This is a great improvement and may server as a solution to #70.
However, despite the setup seems to be working to some degree, there are also fatal blockers: llvm/llvm-project#60063. We should see if we can submit a patch to fix the underlying issue and get remote Windows debugging support