I have done DIY's in Alaska a couple of times, several in various western states, and Texas. Without a doubt the hardest part is making the decision to do it, setting the date, making a commitment to the hunt, and then not backing out; Regardless of the obstacles that might arise (and they have for every participant on every one of my hunts). Finding others that you trust, who possess the needed woodmanship skills, and are willing to make the commitment, is the next hardest part. The research and planning is actually easy compared to making the commitment, finding the people, and then doing it.
My first bowhunting trip to Alaska developed when my brother and I were returning from a Traditional bowhunter of Montana shoot and decided to quit dreaming about an Alaskan hunt and to do it, regardless of whatever obstacles might arise. No excuses! We were going to do it! We made the commitment right then! On the drive home we decided on the species (which we later changed from caribou to moose), the type of hunt (changed form float instead of a drop camp), who we wanted to join us (only one accepted the invitation but the other one got his own partner), and set the date (which was later changed from mid August to mid September). The next day we asked some friends if they wanted to go and after they had committed (a couple of weeks later) the planning started.
You get the idea, the particulars of the plan need to be flexible but the main goal, an Alaskan hunt and date/year stayed the same. After committing to the hunt, at least for everybody I know who has done a self guided Alaskan hunt, the year set for the hunt is paramount, usually nine months to a year and a half from the time you make the commitment to the hunt. Less then nine months and it is hard to make the plans and get the savings/financing together, any longer then a year and half usually results in some/most of the members backing out for unforeseen reasons/problems (if the hunt isn’t cancelled), resulting the final members being completely different from the original group.
There are a lot of things that affect an Alaskan hunt, much of which you have no control over, but if you are willing to make the commitment, set the date, pick the right people, and like the old Nike commercial said, JUST DO IT, it can be one of the best adventures of your life.