Hard to answer the original questions directly... Some general answers: I've not taken either of my Savages on any long road trips. Probably never will, as I don't deem them or myself fit for such. These bikes (87 and 99) are happiest in the 55-60mph range, but capable of cruising at 70+ if you are tolerant of it. I'm not without a windshield any more, and neither of my Savages have one. Hence, longest stretch of 'slab' at or about 70mph so far is probably about 50 miles. I'd rather ride the back roads.
My typical riding is just heading out with no particular place to go. Often turning down roads I notice, just because "I've never been down that one before." This is also typical of me, as I did the same on foot and bicycle as a kid. No telling how far from home I'll roam on any given trip when I do that. I also have some standard 'circuits' of two-lane blacktop close to home that I run around for short occasional rides. Sometimes those rides are as little as 10-25 miles just to break boredom. These rides are usually in the 30 to 60mph range, and can be ridden either at leisure or more aggressively depending on my state of mind. Sometimes I just want to putt along, and might stop just to have a smoke and moo back at the cows
Other times I feel like riding the piss out of the poor little Savages, and scrubbing some rubber off the tires here and there!
I know I've ridden the tank from full to empty in one sitting many times, several times on each bike. And then some more on the way home. But I've never been more than two tanks from home and back, so that means no trips over 200 miles in a day yet. Probably a bit over 150 in a day has happened a few times, and that is plenty to wear me out, and make the butt plenty sore, whether it is the shaved foam stock seat on the 99, or the Sportster seat on the 87. As some have mentioned, the miles get easier on the butt the more you ride, but the Savage's cramped riding position and seat position still isn't the best suited for 5' 10"+ and 250+ pounds.
Only been caught out in the heavy rain twice on the Savages. Once about 30 miles from home, and wearing only a light shirt in cool (60s?) weather. 60s feels like 40s when you are wet and moving 40+mph! The other time I got caught in the rain, I had on my full riding gear, but had no rain suit with me. (I need to buy and carry a rain suit, as should any real biker.) Had to ride about 10 miles home in the driving rain. It was a real toad floater, and I had to ride a two-lane blacktop home with cars and trucks smothering me with tire wash very often. That sucked. My overalls and jacket felt like they weighed about 50 pounds when I got back home and dismounted the bike.
Like I said: Not easy to answer all the original questions straight out, what with my type of riding. But within the above, all the questions are answered in one way or another.
Addition: Thought I'd mention that; though I've only ridden the two Savages less than 3k miles since starting back riding this time, I've not had a road-stranding failure of any kind on the yet. They've been extremely bulletproof compared to many other bikes I've owned over the years. Rivaling my favored Yamaha bikes from the past in reliability. That's pretty good in my book.