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I think your assumptions are sound.
Seems to me, it would be like owning both a Chief and a Scout...I have 2 bikes, and it's hard to decide which to ride, on a daily basis. I've put about 1,000 on the "W" this year, so far, and 8,300 on the Drifter. I love 'em both, but the Drifter is the one I ride most of the time since I do lots of miles "just for the Hell of it". If I'm specifically looking at doing twistys, then the "W" is the weapon of choice. The Drifter has weather protection, and pretty good luggage capacity, so It's the one for the grocery shopping trips. The "W" has a bubble nose fairing, just to keep the wind off your chest, and small bags
The carrying capacity isn't nearly as good, so I don't use it for shopping trips, unless I know I won't be getting a lot...BUT..I can see that having two Drifters with nearly identical abilities would make for a more difficult choice..
I'm thinking of making a purchase, and I know there are a lot of people out there who know a heck of a lot more than I do, so hoping some of that wisdom could help me from doing something dumb, if I were getting ready to. 
I'm thinking I'm ready to start looking for a 1500. I love my 800, but I think I think the 1500 will be better for the following reasons: 1) riding 2-up with the Missus, (approx 350lb combined weight) 2) longer distance rides - I would like to do more long distance. The 800 is great, and I know there are things I could do to make it better, like adding lowers, but it seems to me the bigger bike would inherently perform better on longer trips.
Am I wrong on any of these assumptions? I don't want to be disappointed...
I know there's things I like about my 800 - Ideally I'd like to have one of each....
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