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In this case it's the "hours to days", check steam's download manager if dfhack is in the queue and double-check that both the game and dfhack are in the same beta status (no beta for both or beta for both).
You should also verify the game's files (and dfhack's) through the settings of the game in your steam library as it fixes weird issues quite often as well.
Other than that though, not sure what a windows (or whatever other OS) update would have to do with the game and dfhack no longer running properly.
There should be a file called "stderr.log" in your install folder that would have the errors for dfhack so that file could have more details.