I can't think of any reason to NOT charge to 100% if you are driving out of town as long as you don't let the car sit at 100% for a long time before leaving town or you have to leave right away and the car hasn't finished charging to 100%.
I tend to address this a lot -- you shouldn't get the expectation that you *must* leave within 15 seconds of the car showing "charge complete" to 100% for battery health. I have charged to 100% before in the morning and left in the evening; I'm not afraid to range (100%) charge; and I've even forgotten to set it back to 90% before so that my car sits at 100% for a couple of days.
Once you've checked that your setting is truly at 100% (all the way to the right), the reason the bar doesn't show completely full is that after a charge, there is what we call "vampire drain" because the car's electronics still draw power. Over a couple of hours, you'll see the car move down a mile or so.
There are plenty of threads that give tips on how to maximize range. 165 miles should be easily doable on a full charge of 240+ miles. If the trip computer shows you as being in the danger range, slow down just a bit.