The fact you're considering says to me you may be ready to make a switch. The LT (my 2nd) still stirs me like no other bike I've had/ have. It's not that it has a soul, but it seems alive and has spirit... hard to describe... I guess an example is everytime I go to the garage, I can't help but enjoy it (looking, inspecting, etc). Other bikes I've had, the novelty wears off, or I just don't feel like riding it every day (rain, snow, whatever, doesn't matter). I can't wait to get on the LT. And I don't feel the desire or need to replace this bike with anything else (I'd like to have other bikes, but this one has to stay).
1. What are they like when fully loaded, two up and the asphalt isn'tt the best. It's fine 2-up, on any asphalt and hard packed gravel/ dirt.
2. Does the motor (torque) and gear box (ratios) allow the bike to be ridden at a low speeds through the hills (without excessive clutch work) ? Low speeds are fine, but as has been said, you need to learn to ride this bike- high rpm's! Powerband is in the 4600-5600ish rpm range. It really took me a while to get my head around this and use it. Huge difference in handling and confidence, especially in the twisties. I usually never let rpm's drop below 3800 or so now, unless I'm putting down a highway in 5th, which is what 5th (overdrive) is really for. The bike will sing like a sport bike when you're riding it in range which may take some getting used to coming from an HD.
How about starting on steep grades when fully loaded. Gotta rev that clutch. This will put some wear on it, no doubt, but I've never stalled it. Depending on the grade, I still hate the start from a dead stop.
3. What do you think of the seating position for long rides? My wife and I have never had problems or complaints about the seat. Comfy. I'm 6'1", 180 and wife is 5'3" and under 135
Are the highway pegs comfortable? Don't know, they look uncomfortable. I've placed my feet on the tip wings on longer rides just to try it and I agree with you, it is way too wide for comfort.
4. What do your passengers say about their seats and riding positions? She has never complained.
5. What is the average gas mileage and cruising range? 42 mpg's, consistently over time. I usually top off near 200 or more. My riding style- I usually run slightly faster than traffic on highways (just feel it's safer... proactive), so on highways (which is 30 miles of my daily commute) I'm usually at, near, or slightly over 74-80. In town, I go with the flow. On country roads, I cannot follow any cages for too long (if there is room to pass) so I pass and jet ahead as soon as I'm safely able.
On dropping the bike. I dropped my first one (year 2000-2001) about 3 times, always slow speed or from dead stop. Wife was on once or twice. We both just stepped off and I'd pick it up. At the time, Ihad not riddeen for many years so it took me a while to get the confidence/ skills back to some degree. You may not have any problems in this area.
Dropped the one I have now once because of carelessness/ tiredness/ stupidity. We had just left a park we visited in upper VA and the wife says "I didn't get a picture of the sign." So, on a 2-lane country road that is on an uphill grade with the road sloping down to the right, I attempt to do a u-turn. Saw I wasn't gonna make it, so I stop and start to back her up... and before I could realize there was no road under my left foot (due to the slope and grade) she starts to go down... so I rev to get out of the fall... but all that did was pull the bike forward slightly and drop her on the left side. Pinned my wife's leg- I thought for sure it was crushed. Somehow I managed to lift it (even though it's nose was pointing down hill) off LaNett's leg and LaNett pulled out. Found that her leg didn't get crushed at all, it was simply trapped in the curve of the saddlebag under the muffler cover- the muffler cover snagged her boot. When I got the bike lifted (with help this time) I was amazed to find the only scratch is under the left tip-over wing. No chrome off the saddlebags or any other plastic got damaged- that is remarkable. EDIT: I should add, LaNett has never expressed fear to get back on.
So, with all that said, I suggest you not test ride one until you are ready to make the switch. Good luck!