In my previous post I was at work, more time now! Skip, as you know the Vintage is a better touring bike then the Bobber will ever be. As I own both, I feel I can give an objective answer.
I have done (2) 400 mile trips on the Bobber. Firstly, fuel management is important, the Bobber has a very cool looking but small tank! I always show up for a ride with a full tank. By myself it's not an issue. When riding with an Indian group they are usually a "mature" bunch and do a comfort stop in less then 2 hours, so not a problem. If there are Scouts in the group they have to stop anyway. If it's my Harley buddies some are in their mid 20s or thirties but they go less far then the Indian riders and if there is a Sporty in the group they have to stop anyway!
Comfort wise you need to try it for yourself. If you don't like the bars or seat or whatever just remember Triumph makes over 150 accessories and the aftermarket is growing daily. The stock seat is comfortable and so is the Quilted, stay away from the Statement seat, you will pay for that cool look, I have all three. The seat is adjustable forward or back and goes down as it goes back. The optional Apehanger bars are super comfortable for me, as they are for many!
The Bobber handling is great. My Harley buddies don't want to get off the thing, it's a gas to ride. 90 HP bicycle is the most common quote, everyone is smiling when they come back! If you are near the 185 lb target weight of the stock shock you mite be fine. If you are a big lad then the optional Fox shock or a Matrix may be better , they are fully adjustable, but expensive. You will not get the "riding on a cloud feel " of the Vintage though! You will love that Triumph accessories are about a third of the cost of Indians.
Every year the Vintage gets harder to maneuver around the garage with cars, other bikes etc., Not so the much lighter Bobber.
Everyone compliments the Bobbers looks and thinks is is a meticulous restoration, much more so then the Indian! When we were at the bottom of Mt Equinox I was parked next to my buddies $40K RM Elite and about 3 people walking by said "gorgeous Triumph" I was embarrassed for him!
In short the Bobber is just a super fun ride. I have a great bunch of bikes in the garage that have mostly sat since I bought the Bobber! Give it a test ride!