I have the latest Windows insiders build on a spare machine. I've found all the aws tooling including SAM works pretty well under WSL 2 now that WSL uses a true Linux kernel.

Tried getting SAM to work on OS X, no luck, lots of pain.

True.

I stopped using windows for dev machines long time ago, but I'd guess with the Linux subsystem stuff it will catch-up in the next years.

I honestly have no problems developing on windows (except when my macos coworkers dont consider windows). Docker is the only real issue.

Yes, it's unusable on macos and windows.

Hopefully WSL2 will solve this.

Docker largely works fine on macOS? At least for testing, haven't run into any issues other than bad filesystem performance if you're writing a lot of data to a mounted FS. Our team uses it daily - a far cry from "unusable".

Maybe you just got a higher pain tolerance or better machines?