There are tools that should assist you in my article
Maine Challenge Cache Help. If anyone had any ideas that should be added by all means say so and I'll add it.
There is also a GSAK macro titled
CacheRoute which will assist in plotting out the best route for up to 25 locations.
The one thing I'd reccomend to anyone doing the Delorme Challenge if it is at all possible - Don't rush it; it will mean more to have done a few of the tougher caches on some of the grids than grabbing one of the more recently placed "quicker" ones and scurrying off to the next map. There can be some great adventures within the adventure of the challenge itself. Also, while you are out, you may want to verify any of the 2001 caches and attempt those to qualify for the
Cache Like It's 2001 (GC146JV) by
Sudonim (5/5).