You are correct that there are a lot of logistics involved in hunting so far from home, in an area you are not familiar with. For an AK DIY caribou hunt, the biggest pieces of the puzzle (given that you have a hunt partner identified it seems) are:
- Deciding on the type of hunt (road hunt off the Dalton, or flyout via bushplane)
If you opt for a road hunt off the Dalton, are you bowhunting, or doing the 5 mile hike away from the Dalton to get to legal rifle hunting areas?
If you want to do a flyout hunt, finding and booking a reputable or trustworthy transporter is a fair challenge these days. The best or most well known outfits are booked a few years in advance. I would guess that there are a few smaller, reputable outfits that might still have openings, but since they operate mostly by word of mouth, they can be hard to find.
- Planning and accounting for all of the costs associated with the hunt
Once you decide on the type of hunt you want to do, the rough cost framework can be crafted. The Dalton Highway hunt is less expensive than a flyout hunt, and has less logistics that rely on parties other than yourself. But, my sense is that it can be a challenge for a first timer, as finding the caribou, being there in the time window they are moving through the area, learning how to work with the other hunters along the highway (for bowhunters), or finding them after the 5 mile hike (for rifle hunters) are some of the unique challenges that this hunt offers to a first timer.
The remote flyout hunts are more expensive, and offer some different challenges in terms of weight restrictions for hunter and gear, meat/trophy care, and being prepared to handle weather delays that often impact the bush flight schedules.
- Logistics in getting to/from Alaska
Since you are in the St. Louis area, there are probably decent flight options to Seattle that will allow you to connect to a flight to Anchorage or Fairbanks.
- Logistics in getting to your point of entry into the field
If you are doing the Dalton Highway hunt, you can rent a vehicle, although rental options are somewhat limited due to many of the major rental companies not allowing their vehicles to be driven on gravel roads like the Dalton or Denali Highway. Flying into Fairbanks saves about 400 miles of driving as opposed to flying into Anchorage, if the Dalton is your hunt choice.
If you are doing a flyout hunt, you will need to get to wherever the transporter flies hunters into the field. That could be a remote Alaskan village, which would require another connecting flight from Anchorage or Fairbanks; driving to the airstrip if the transporter is based somewhere along the road system; or getting to the airport or lake if you book a transporter out of Anchorage or Fairbanks.
There are lots of other logistics (meat and trophy care, knowing the specific regulations for the area you are hunting, etc.) but most of those will be derived from the type of hunt you select, and the location you fly into and out of while in Alaska.