I don't drive anywhere near that much, but this is almost certainly fine. For a 300 mile trip, if you charge to 90% before you start (with an L2 charger like in your garage), you can get most of the way to where you're going, and charge at the last Supercharger along your route for just long enough to use the facilities (like, 5 minutes or so). That'll get you back up around 40% and you can be on your way. Then L2 charge at the destination. You're never charging to a very high state of charge with the fast charging, so it will have very little effect on your battery life. I aim to get home with ~20% or so, and slow charge from there (also home electricity is cheaper than at a Supercharger).
You might think you should try to charge to 100% before you leave and make the whole trip without supercharging, but that would be more nerve-wracking to you and much worse for the battery.
On average the batteries seem to lose maybe 10% after 150,000 miles, but most of it is near the beginning. It varies quite a bit, but based on the graphs I've seen I wouldn't be surprised if you still have 85% of the original capacity at 300,000 miles.
If anyone here has actual experience with very high mileage, it would be great to hear that!