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Money wasn't an issue for me- but saw no reason for the "extras" on the Ultra. Even after I had the dealer install cruise & the rear tour pack lights for $650, I still saved over $1500 by going with the Classic.
$1500 buys a lot more important things for me than 2 extra speakers, a CB/intercom I'll never use, and fairing lowers that I'd take off 95% of the time.
It all comes down to what you want, what you need, and what you're willing to pay for...
I'd have to agree with those that said Ultra. I know I once didn't have my cell phone with me and suffered two flat tires at 2 a.m. I'd have been their for god knows how long, but was able to issue a mayday on my CB and even at 2 a.m. someone was monitoring the emergency channel. Most may not be needing the CB... but out on the open road... you become operationally ineffective... the one time you need it, you'll be incredibly glad you had it. Plus all the other great things that come canned with the bike... their really is not much of a choice in my book... especially if you are going to be doing any distance. Which even if you don't now... with one of these things you will grow into it. I've never ridden a bike that just didn't ever want to stop. Takes me over an hour to get to the office one way... but its the shortest two to three hours of the day.
I got a classic in Luxury Blue and silver, not my first choice, but when you buy used low miles and and unmolested bike take presidenc. I got mine with 4k miles. I still would prefer black, but I do like the ride and the tunes.
If you ride with a group, 3 or more bikes, it's great to communicate on long trips. We work the lead and tail gunner system where the lead communicates all turns to the tail gunner. Additionally, when separated in traffic, it's easier to keep up with one another. if you want any of the Ultra goodies, it's a whole lot cheaper to buy the Ultra to start with than add the additonal items.
Classic all the way. Don't like the looks and wouldn't use lowers, would never use cb (have cell phone), remove that damn tour pack and huge padded seat when the babe isn't back there, throw on the low profile tinted windshield, go billet light bars etc, and you have one bad looking bike.
Hint, spend the extra money required to purchase the Utlra for the above extras and cruz control and you'll have the best of both worlds.Don't get me wrong the 4" padded seat and tour pack are nice for long trips, but I like the looks of the bike without them.
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