I went from a 05 fat boy to a 16 ultra classic. I found the ride and handling is much better. But the weight is a big difference along with seat height. I don't know what you want to spend, but I would want a 14 or later just because of the navigation and radio. Good luck

Here's what I went to. Love everything but the weight.

 

Thanks for all the input!

The bike is priced at $8,995. I would be trading my Fatboy in and hopefully coming out on top. But I have yet to even talk to the dealer to see what kind of deal I could make. I would love to have a 103 (what my Fatboy has) but I don't think my budget will allow that. In the end I might end up keeping the Fatboy a little while longer until I can afford something newer with less miles and a 103 if possible.

As for the mileage, I was kind of thinking what was said above, if it has had any issues I would think they have already been addressed. And if I would get it and end up needing major work down the road it would be the perfect time to step it up to a 103. But right now it's just an idea for me. I'll decide once I see it in person and see how it runs.
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I just picked up a 09 UC two weeks ago at a Honda dealer. 18K on the clock, all the service receipts and add-on receipts. Paid $9250 all in. Bike has true duels, PCV tuner, slip-ons and several add-on goodies. Clean as a pin and runs great.

 

Too many miles on that bike...let somebody else buy it that is looking to make a redo on it.
If you are looking at getting into an Ultra Classic, coming from a 2012 Fatboy w/103, I'd look at a 2014 with the 103. Also, the 2014 had CB as standard too, plus the Boom Box radio Navigation system.
Going from a 2012 Fatboy to a 2009 Ultra Classic is stepping backwards in time. You're spending your money foolishly, in my opinion.

 

IMHO, if you're looking for a 'gas and go' ride, I would look for something with fewer miles on it. Try to find the newest one with the lowest miles you can afford. It's a buyers market right now, so you should be able to find a deal. I would suggest traveling (500 miles +) to get the right one or even consider shipping. Just my .02

 

those who are sell high mileage bikes ( 75k is high ) always say "dont worry about the milage". typically you can find low mileage harley's for a fair price.

 

Mean City Cycle will take care of that seat for you. I my self wouldn't even bother with other seats like saddle man and such. but sometimes you can find used ones for a good price.

 

I'll confuse you even more and go the other route. Used bikes depend solely on if they speak to you or not. If you walk up to it and you love it and the price seems fair, go for it. If there is any hesitation or second thoughts when you see it, walk away and look for one that puts a big smile on your face when you first see it.

As far as the mileage goes, older bikes with low mileage scare me more than the one's with what other people say is high mileage. An 09 with less than 20,000 miles on it means it has spent a long time in the garage and short bar hopping. Some of those bikes still have the original tires which at 9 years old are a ticking time bomb. The seals are probably dry and waiting for leaks. "Higher mileage" bikes are used regularly and are usually maintained well. The 96 in the 09 is exactly the same as my 08 RK. The engine is good for over 100,000 miles easy. Mine was still running fine at 112,000 miles when I got the itch and the money to upgrade it. Based on the mileage you are putting on your fat boy and expect to put on an Ultra, how long will it take you to get to over 100,000 miles. You have that much time to save for the upgrade. My guess the original owner took good care of it and got the itch for a new bike with the M8 engine and traded up before the mileage got what everyone would consider high.

Your *** can't handle it because your a big guy on a softail. When you get on a touring bike with a fairing, smooth ride, tunes, and hopefully anything but a stock seat, you will be amazed how far you can go between stops. Especially with some foot pegs on the engine guards so you can move your feet around. It's going to be heavier which adds to the smooth ride on the highway. The fairing makes the steering heavier and it will have a higher center of gravity than you are used too but you will get used to all of it fairly quickly. I miss my softail but once I got on a touring model, I'll never look back. You're going to loose some power going from a fatboy with a 103 to an Ultra with a 96 but it will have plenty to go down the highway without a problem.

Good luck on finding a bike that speaks to you.

 

Found out that the original owner had it until 2014 and had it serviced every 5,000 miles. The only work I've found that's been done to it is compensator, regulator, some brake lines, ABS recall, horn relay, derby cover gasket, and oil drain plug seal. Sounds like it's only been a 2 maybe three owner bike and been taken care of. Hopefully I can go look at it tomorrow and get a feel for it. The place that has it says it rides like a bike with half the miles... But of course they're gonna say that so they can sell it haha. Guess I'll just have to wait and see how it is in person.

 

It's so sexy too.. I just can't decide if I want to buy it or not. I can get an extended warranty on it. But I have to put a tire on my Fatboy to get a straight trade... Decisions decisions. I also have yet to find another one for sale with the special edition color.