Well, I'm glad you're going to do something good for yourself when you get out of the army.
6 months is a long time - and you haven't indicated your aims or your experience.
From your other posts, it sounds like you have a few others interested.
But it also is a big trip - and some folks may not find it their cup of tea.
Your time frame for the loop you have posted is not the greatest - in some places just plain bad.
You've got yourself in the Northern Tier in late April/early May and it can still be pretty cold and wet.
Similarly, you have yourself in the Southwest desert during the hottest time of the year.
I'm sure you can survive it - but you've probably been "surviving" for the past year or so.
Not to mention that the Northern Rockies still have lots of snow in May/early June.
The route you have outlined works best with an early May start.
The time frame you have - March 15 to Sept 15 - works best if you start further West.
In fact, if this winter is rainy out in California - the deserts should be blooming in March/April.
Southern Tier/Route 66 to the Mississippi River then north and the loop to S.F. and Western Express.
It's hard to come up with a good loop starting in St. Augs in mid-March.
Either you go clockwise - i.e. west - and end up the wrong way on the Pacific Coast -
Or you get into chilly wet weather if you head north too soon.
Here's Prism's climate website with monthly temp and precip maps.http://www.prism.oregonstate.edu/
PS - Nothing says you have to stick to ACA maps.
They are good - esp. at first - but no need to limit your possibilities once you get used to riding.