Flow: There isn't a clean way to keep an exe running all the time. o_dog is right, something like firedaemon or the free MS anysrv(?) can be used to do it. Neither will catch the program locking up like a true service might, but they should work.
Alternatively you can use a .exe or TCL wrapper run via the scheduler on a periodic basis to see if something is running and restart it if necessary. I should probably add on the wishlist a scheduler feature for items scheduled as * * * * to just start at runtime and restart if they fail. The problem with something like that is if the server itself crashed or was brought down and the exe kept running how/when should you stop it? Or should it even be stopped? What about when the server is started again? There isn't one correct answer, but any logic to do that kind of stuff would require a middleman if you want to run an off the shelf thing like eggdrop.
Of course if you have to have a middleman anyway creating the simple app and tieing it to a site command and a periodic scheduler event seems pretty easy and wouldn't require any server changes to do.
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