I’m sort of an automation junkie but it can be difficult and thing tends not to work as planned without a lot of experimentation and hair pulling. I would suggest creating a bare bones mod that you can play - albeit cumbersome - and then work on automating a few items here and there. Having said that…
I created a dice rolling scheme as a sample mod for another designer which is quite similar to what you’re looking for. You may be able to glean some information from that. Here’s the thread with the attached sample:
[url]https://forum.vassalengine.org/t/a-complex-dice-rolling-problem/3422/1]
May be able to give you some advice on the other things but I’ve got to run right now.