I'm not a hardcore, life-long IBA rider, but I've got a couple of rides under my belt. Take my suggestions knowing that. Phones can be finicky. GPS trackers are easy to mess up, especially when you're excited about getting started with your first long distance ride. Go ahead, ask me how I know. You'll want a DBR at the start, end, and every corner of your route. You'll get fewer miles if your GPS tracker doesn't track you and you don't have a DBR from the East side of Waukesha. Going around the west side instead will cost you 6 miles, on an already tight run. If you then forget to stop in Fort Smith, you're toast. At the end of a long ride when you are sore and all you want to do is get the ride over, it's easy to forget about a backtracking detour like that.
Your proposed route has you hitting I-94 and changing directions shortly after starting. I'd suggest a DBR there. But you just got on the road and would be stopping, which eats up some time. Why not officially start the route there, at I-94? That way you'll fill up and hop on the interstate to start eating up miles as fast as reasonably possible. Then, since you're on the interstate system, stick with it. Instead of getting off the interstates and on smaller state highways at Madison, take I-90 over to I-35. Get a DBR at that corner then head south. There's a Love's Travel Stop at that corner. They make great bathroom and fuel stops. They give good DBRs, are clean, and always have food if you're hungry. Love's is a go-to stop for me. From there, I-35 down to Kansas City. Flow right onto I-49 there and head to I-40 near Fort Smith like you originally planned, but skip the Pizza detour. Southwest of Little Rock, where I-430 meets I-30, there's another Love's. That will make a great end point for your ride. It will be 1079 miles, so a much better cushion in case of GPS tracking errors and unexpected route changes or any other weirdness like that. It will add about 20 minutes to the time though, so that's something to consider. If need be, there's a Super 8 hotel that you can probably see from the Love's parking lot. Get a hotel room, a nice hot shower, and some shut eye before heading home the next day. I know you'll be close to home, but with the excitement of finishing the ride over, that can be a dangerous 20 minutes. It's better to just stop and pay another $50 for a cheap hotel room than to risk falling asleep on the way home. That's something you'll have to figure out when you're there.
Also, since this is your first long distance ride, you can cut it short at the Valero in Conway where I-40 heads south to Little Rock. There's a hotel you can probably see from the parking lot there too. It's 1,045 miles, which I think is perfect. It's also 10 minutes faster than your original route. The downside is that you're a little farther from home when you end the ride. If you are tired and get a hotel room, that doesn't matter at all. Another few miles on the ride home after some sleep is nothing. If you're not tired and continue home after the ride, well, it also doesn't matter because you're not tired.
Here's a link to the route I'd use. Also, I'll be in Hot Springs for another week and a half, maybe two weeks. If you make the ride during that time and need an end witness, hit me up. I'm a night owl, so I don't mind meeting you at 2am if you need a witness and don't want to start hitting up complete strangers. Good luck!
(Edit) A little bit more time spent playing with your route shows
this route. 16 hours and 1,044 miles. Same start and end points. Better cushion, no backtracking, but it does have tolls according to Googlemaps. Might be worth considering.
