This is a seemingly civilized configuration - to my unix-biased way of thinking - as cygwin gives me a shell and ssh is a very familiar way to access machines for logins and automation.
Unfortunately, Windows has a very complex permissions scheme (ACLs) and cygwin+openssh+scp just won't honor Windows permissions. No matter how I tried, the files would land on the server without properly inheriting the permissions of the directories they landed in.
Luckily, Windows provides a relatively easy way to fix this problem in the utility cacls.
What I ended up doing was using cacls with the '/S' switch to get the string representation of the parent directory of the location I copied files to, then used the '/S:
You can use the nifty "AccessEnum" utility (google it) to verify your permissions a lot more quickly than a ton of right-click/sharing-tab examinations.
Poof, perfectly consistent permissions.
I'll continue choosing unix for my servers though, thank you...