Thank you all for your input! It's really helpful! I agree with all of you, and didn't realize that I was already accidentally taking into account
@stevezzzz comments about coating to too-high speeds. I hate getting pulled over for speeding (takes you longer to reach your destination than if you had been going slower, and point suck). I already started driving slower when we got the Prius (being replaced with my future S60D), and even more so when we got the LEAF (the car I predominantly drive). So I'm usually at 55 mph at the top of regular hills, and at 50 mph when I reach the top of a big hill (there's one I allow myself to slow to just over 45 because you gain back so much speed on the other side). I then coast down and will start regenerating if my speed gets between 75 and 80 mph (for safety and to avoid getting pulled over). So I incidentally never had to worry about drag at 100+ mph.
@jerry33, I completely agree with taking it slow and relaxing. I didn't realize the benefit until I started doing 55 mph on the highway in the LEAF. I don't have to be on constant vigilance like I did when trying to maintain 65 and continually trying to pass people. Now I get to enjoy my surroundings and whatever music I'm listening to. I think I can make to to Lake George in one shot in all but the winter, even accounting for the extra weight, since I take it slow. Though I might have to start following trucks again.
I'm really looking forward to seeing what mileage I can get in the S60D. I realize the increase in weight from the LEAF means my numbers will take a hit, but that gives me a goal to reach. I want to try and at least hit my cold-weather LEAF average of 4.2 mi/kWh (238 Wh/mi) as my warm-weather Tesla average, and try to hit or beat 4.0 mi/kWh for long highway trips in warm weather. And winter might not be too bad if I preheat the car. It was close to or at single digits when we test drove the MS this past February, and with my wife and two kids in the car with me creating extra body heat, we pretty much only needed the seat warmers. So I think we'll be able to only use heat intermittently when going up to Lake George just to keep our feet warm. That's really the only part of me that gets cold when driving the LEAF without heat in the winter. Hat, leather mittens, earmuffs, and seat and steering-wheel heaters take care of everything else. I fully realize though that my 5.0+ mi/kWh (200 Wh/mi) warm-weather local driving average is pretty much a pipe dream in the MS. The real trick in the winter will be seeing what snowboards on the roof will do to the range. I'm hoping to at least make it the 159 miles to the Albany SpC station in one shot, though I realize I may have to stop at the one in Newburgh first.
As for my mom, she's a bit stuck in her ways at age 71. So i just need to determine what EPA range they'll need in order to make it up in one shot in the winter (she might be willing to get off at Albany and charge it it would only take 10 minutes to get enough juice for the last 55 miles or so).
And yes, I have destination charging. Not ideal (just a regular outside outlet right now), but they're looking into getting a 50amp, 240-volt outlet installed. Either way, since we always stay at least one night when we go up, even a trickle charge would be enough to get us back to Albany on the way home. Strike that, just looked at the SpC map and Tesla just added one in Queensbury in the last couple of days, which is right by my parent's place in Lake George! In fact, it's right by the entrance we use to get onto I-87 to come home! Score!