I like to get dates figured out way in advance, or it never fails someone in the group will require a weird date, then decide to not even show up, but we’ll be locked into the date or the hunt area.
If the trip is really important to me I’ll plan it and tell the others they are welcome to come a long, but the trip details are set in stone.
I’ll have an equipment list of what I’m bringing (my standard check list so nothing is forgotten) and any must haves or things to avoid for others.
Many like to research online, but I still like paper maps to be able to visualize the areas better. BLM and FS maps are my favorite. I still have a printed road atlas for planning.
For specific travel and misc details while on the road I think in terms of what’s being done each day and can write everything for that day on one sheet of paper for one person or 20. The more you do it, the easier it gets.
I’ll throw out the itinerary I like to the group, along with snapshots of maps, motel reviews, meal ideas. If someone has a better idea, or it makes people happy it’s not a big deal to me if we eat at a nicer or cheaper restaurant, or if we take a more northern or southern route. I do have a hard stop after 12 hours of travel.
As for specific hunt areas, I don’t pay much attention to odds - I’m partial to specific areas and if those don’t get drawn I’d rather not go to a mediocre spot. Hunting a new area in itself is a big warning that it’s going to be harder than it has to be.
For the most complicated situations I’ll pin up maps, itineraries, photos, etc on a war room wall. In my obsessive mule deer days I had a pretty good section of NW Wyoming maps on the wall all year and as information came in I’d add post it notes.
I’ve made a good size dry erase board for important dates and whatnot, but other years I’ve been happy with a spreadsheet. My brain visualizes better if it’s on a wall.
At one time I had every BLM and FS map for all of Wyoming in a travel bag. Our local college library had all the topo quads for the entire state.
Over time many things become second nature - when a friend wants to hunt a certain area, within seconds I’ve visualized the route and roughly what the country looks like. Within minutes the odds, hunting pressure and dates start to sink in. Usually I’ll not want to make it “our” trip - he can figure out what he’s happy with and I’ll go along, maybe in my own rig if his plan sucks.