Pirate, I use the Bubbler GPS Pro on my phone connected to a Spotwalla account, which also allows me to have an "At-home" safety over-watch. I set it up so either my wife or Mother-in-Law can watch our trip progress live on a computer screen and would know when an un-planned stop (or crash) might have happened. The Pro version allows more frequent updates and some other nice to have features.
My first BB 1500 was completed in 30 hrs, 20 mins and we weren't trying for a BB Silver even.
This included a restaurant stop for Lunch, Dinner, and Breakfast, with a couple 20 minute+ naps (on the spyder). 90% Interstate, I can relate to the Pay at the Pump issues, been there done that. You doing it on a triple should be easy enough with good rest before and after. We did it on 2 Spyders and felt safe all the way.
I can imagine older folks wouldn't feel that way. Shoot the IBA just announced a Seniors Rally for this year. Unfortunately I don't qualify.
Ignore the naysayers, they just don't get it. Go for it. Send me a link to your Spotwalla trip before you go.