Just use ssh from Cygwin. DLL hell was rarely a problem, just always install everything via setup.exe.

The single biggest problem it has is slow forking. I learned to write my scripts in pure bash as much as possible, or as a composition of streaming executables, and avoid executing an executable per line of input or similar.

Slow forking is only the second biggest problem IMO. The biggest is the lack of proper signals. There's a bunch of software out there that just isn't architected to work well without non-cooperative preemption.