After doing the map below and some calculations, I determined that I will need to depart on my trip on April 25th in order to possibly be in South Dakota by my family reunion (or Mom's birthday) in June. I expect this trip to take about 4 months. I could probably do it in slightly less time but I want to actually enjoy the ride rather than just get from here to there.

After a lot of thought, I have decided I am going to do the ride this year. You can read some of my thoughts about the decision here. Meanwhile, I have also changed the route a bit and I'm calling this trip "The Sibling Tour" because I will visit all my 6 siblings on the way. One sister near Lincoln, NE, my only brother in Harold, SD, 2 other sisters in Fort Pierre, SD - a sister in Gillette, WY and finally a sister near Seattle, WA. Here is the proposed map.