faster92... I can give you my opinion...and that's all it is. I'm not an expert opinion giver. I'm a guy that's not into POWER or excessive SPEED. I love to ride, I love to travel and I love gadgets. I presently own a 2012 XCT that I purchased in October 2011. I have test rode a 2009 Ultra, 2010 and a 2011 Ultra. I have test rode a 2014 Indian Chieftain 2 times. So that is the extent of my expertise. Here are my observations in REVERSE order of preference.
Harley Ultra Classics - I have rode 3 years worth of these bikes. And while the test rides usually comprised of an 8-10 mile ride, each time I rode I was disappointed (and one these times is when I owned a 2009 Venture that was a BEAST).
Harley Ultra Classic
Pros - Lots of low end torque
Lots of colors
Lots of bling
Lots of options
Cons - Hard riding
Uncomfortable ride, cramped (and I'm short).
Lots of vibration (some may like that, I don't)
Handling was only fair
2014 Indian Chieftain
Pros - Lots of low end torque (more than the Harley)
Tradition (and traditional colors)
Remote Locking Bags and Remote Start
Adjustable power windshield (that's a big one).
Blue Tooth and TPMS built in
More comfortable ride than the Harley
LOTS of gadgets on the bike
Cons - Still a little cramped
Better handling than the Harley, but not as good as the XCT
No touring trunk (I know, an Indian may not look good).
Vibration (not as bad as the HD), which effects the windshield.
Cross Country Tour
Pros - Handling, Handling, Handling
Proven engine reliability
More storage than any other touring bike in the market
LOTS of leg room
Room to grow with engine performance (for some)
Handling, Handling, Handling
Cons - No power windshield!
Hot in the box (Cockpit can get pretty toasty in the summer)
No tradition (yet).
Obviously, I am biased. I love my Vic. NO BIKE IS PERFECT. On any bike there will be pros and cons...it whatever pros fit you best and whatever cons you can learn to live with...for me, I'm a XCT fan all the way.
I am NOT interested in test riding another Harley...and I truly wanted to like, love, own an Indian. And I did LIKE the Indian, I just didn't love it and it didn't FIT my style of riding.
Now the rest is up to you...take in what everyone has to say and focus on some of those tips, points, pros and cons and PULL THE FRICKEN TRIGGER.