06z, I applaud your "mission awareness". I wish more people would make a good effort to understand what an EV can and cannot do for them before they purchase.
That said, I'm a little surprised the DSR couldn't do the trip you asked of it. My daily round-trip is ~43 miles, I'm heavier than you (I'm a big guy, over 300#), and I regularly get home on my 2014 SR with more than 50% SoC left. Granted, I only have one medium-sized hill to climb, and you have a little more mileage than I do. How much of your ride is at freeway speeds? Mine is around 50% freeway speeds. That could make a big difference.
My first comment would be, don't underestimate the increased range you'd get with a good fairing/windscreen. I got more than a 20% range improvement when I installed mine. Ditto for reducing speed -- the speed vs drag curve is exponential with a big exponent (at least cubed). I keep my bike in sport mode, but exercise some restraint with my right wrist to keep my freeway speed between 70 and 75 most of the time. Also keep in mind that the faster your speed, the more effect a good fairing's going to have.
I was a little concerned about range before I bought my bike, and my local dealer wouldn't let me borrow it for a day to find out. At the time I was using mostly the freeway, about 50 miles round-trip. So after I bought the bike, the first day I rode to work, I kept the speed way down, no more than 65 on the freeway, and made it home with (IIRC) around 35% charge left. I increased my cruising speed to 70, and was still getting home with better than 20% left, which was my threshold for being worried about it. I was happy with that...but then I bought and installed my windshield, and things picked up considerably. I quickly found out that I could cruise as high as 75, which is about as fast as I generally want to cruise on the freeway anyhow, and I'd get home with 30% or more left.
Since that time, my battery was replaced with the 2016 version (which is 13kWh instead of the 11.4kWh I had), and I've found routes that get me off the freeway more both on the way to work and on my way home. Time spent is about the same, but the mileage is shorter and the speed is lower, which increases my range. I now do about 43 miles per day, and regularly get home with 50-55% battery capacity left. It makes a big difference when I have errands to run after work.