Things that were going to be challenges on the route:

Just picking a start took a month.  I knew that I wanted the start to have lots of places to stay and to have a 24 hour place to sit down and eat at the end.  In Minnesota, that's a challenge right there.  I finally settled on Stillwater.  There, I found a cluster of inexpensive hotels next to a Perkins.  Stillwater itself is also quite historic and charming, despite the fact that Michele Bachman lives there and she and I are something like Jesus and the anti-Christ (if you live in Minnesota, feel free to pick which one you think is which).  Stillwater is one of the first towns in Minnesota, right on the St Croix River and, like Duluth, has a working lift bridge.  It also has some very charming neighborhoods and parks.

There are about 20 different routes in and out of Stillwater and I quickly settled on one that would avoid taking riders down the enormous bluff it is built on.  But there are still quite a few beautiful and historic houses.  The best ice cream stand in the town is also on the route for the return.  Yes, I think of such things when doing a route.  I also wanted to avoid busy streets like Main St/MN95.  Though the view of the lift bridge is nice, the lights and chaos are not so good.  I was able to capitalize on a flèche route from a couple years previous and use backroads along the St Croix River from tiny Taylors Falls to Sunrise and avoid much of busy 61 using quiet Government Road, which has technically been a road for over 140 years.  These towns are all mom and pop, not a chain in sight and have interesting architecture.  They harken back to the days when Minnesota was fur trapping territory, the true frontier.  No busy roads and smooth pavement - so far so good.  The first 200k was done.

The Munger Trail went from Hinckley 70 miles to Duluth.  This was an easy pick.  Towns abound on the trail, cell phones work due to the proximity of I35.  Sure you had to get to 35 to find anything 24 hour, but that works out okay going up.  Off route 2-3 miles isn't unreasonable for the way back, that would only be an issue for people trying for a sub 24 and this wasn't going to be a great route for them to start.  The trail takes an old railroad bed down into Duluth, a gentle grade when every other option is quite steep.  Perfect and scenic - this was to be a big highlight of the ride.

Getting across Duluth turned out to be a months long process of experimentation.  I did this section over and over bringing different people with me.  Big thanks to Gary, GearBob, and the only other Minnesota Randonnuese to ever complete PBP, Lara.  It was really quite interesting to see how the different people had different priorities.  GearBob and I tried Lara's very direct route through downtown.  Some quite nasty sections that conceivably could lead a sleepy randonneur onto I35 on the return gave us pause.  Gary and I did another route that while nice and direct, went through a crack neighborhood.  I saw 2 drug deals, a guy getting arrested and a guy crushing for a prostitute all in about 6 blocks.  Gary noticed none of this, but I have to admit the cue sheet would have been simple.  I saw myself sitting at a traffic light in the dark and decided that rider safety would overrule.  We would have missed the Lakewalk too.  The Munger Inn, right at the end of the trail, would make an excellent overnight keeping most of the night riding on a bike trail.

So in the end, GearBob's route prevailed.  We avoided most traffic lights and kept off the major streets to get to Canal Park and the lift bridge.  From there, a ride right on the boardwalk next to a still running old time train and spectacular views.  The cuing was exceedingly difficult though.  Getting every cue to be concise and clear took a huge amount of effort.  Not perfect and speed demons would be annoyed, but there you go.  The turnaround, at Two Harbors, would have ample supplies.

The return, I reasoned would be exactly the same up to Hinckley.  There, we would opt for straight down 61.  This gave me the requisite 600k and provided 24 hour services in Pine City and North Branch.  Not as scenic, but pretty flat and on day 2 everyone is tired anyway and wants to get home.

I reasoned many might want to pre ride parts of this route, so I chopped it into 3 parts of about 200k each and submitted them as permanents.  That was in May and the route was ready to go 4 months before the ride.  Plenty of time for me to do several trial runs and triple check the cue sheet for clarity.