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If it were me, I'd break it down to one thing. Is the Heritage doing what I need it to do? If the Heritage is satisfying your current and/or future riding needs then keep it. If you find that it lacks something you think the Ultra can give you, then look closer and try to negotiate a deal you're comfortable with.
Sometimes it's easy to get excited about something just because you know you can have it if you want it.
How old are you because if you're old and need to ride on a sofa it's time to trade up. If you still want a nice looking non-old man bike keep what you got.
And this is coming from someone riding a nightster. Is that your way of saying "I'm a poser that can't handle a big bike so I make disparaging remarks about those that can"? Non-old man bike? Whats that? Is that something like the chick bike you ride?
How old are you because if you're old and need to ride on a sofa it's time to trade up. If you still want a nice looking non-old man bike keep what you got.
It's a process, start with a naked cool loud bike cams,carb and pipes(hey look at me)can't even carry a letter to the P.O. without tucking it in your shirt or sitting on it, basic bar hopper.Move on to storage(ie bags) removable stuff so you can actually carry something more than your ego but still take it off and be cool.Detachable windshield and bitchbar is next find out you can actually accomplish a task run to the grocery store carry a jacket,spare glasses,tools OL don't fly off back. Still need cool factor on weekends.Find out you leave the bags and shield on more often than not bitchbar maybe.Now you hear the motor with the windshield on and think WTF does this bike have any oil in it. Music(for me the greatest thing since sliced bread) solves that problem now your on your way.Pull up next to a gray beard drivin on the interstate doin 80+ on an old man bike his OL onboard relaxing catching rays,his feet on the highway pegs music at concert level waves to you with right hand sittin that sofa seat.
Go with my plan if your age permits: I'm keeping my Heritage for ever, and 9 years from now I figure I'll be old enough to justify a touring bike. By then my bike will be long payed off, and I can just add a good new or used touring bike to the collection. And for any of you that suggested you need a Ultra for any trips longer than 500 miles- go buy yourself a car...
Personally, I think they low-balled you on the trade in price. Ultimately, as many others have said, it's your decision. The UC is an excellent bike for daily commuting, rain or shine. I ride mine year round. But I will be adding another "smaller" bike soon. I'm thinking a used Corss-Bones would fit well. No bags, no rear seat, no radio, no windshield, no frills, just me and the bike. I miss that sometimes.
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