Same problems here, so a couple things I've been mulling to help:
A new order for squads: "Escort outdoor work parties" and a new option "Workers stay indoors unless Escorted". That way I could lose a squad in addition to the woodcutter, hehe.
Maybe conditional/seasonal orders for the Manager or somebody:
-if {wood in pile} less than 15, add 10 woodcut jobs. Or better something like "set the number of open woodcut jobs to 10 if it is less than 10" to avoid repeated jobspamming.
-if {raw webs in pile} more than 4, "set weave silk 4"
or even if {cows > 12 and butcherable corpses < 1} "set butcher oldest cow to 1"
Also it would be nice to have an option for the manager add orders to repeat periodically, like on a specific day of the month or once per season or in a specific month or season, especially for things like "gather webs", "process plants", "weave cloth" etc.
This would go a long way to cut the mundane repetition that's fun and necessary at the beginning but that starts to get in the way of the bigger picture later on.
Oh, also please leave the completed manager orders (but greyed out or have another screen with those), so I can re-issue them quickly with just a click - that would help a bit too.
As a first cut though, some warnings would be handy. Maybe a screen with configurable triggers like "wood below X", "commodity Y below X", "fewer than X designated trees", "less than X free Y pile space", "more than X butcherable animals"?