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Yeah, putting miles on it can interfere with other obligations and responsibilities!
Actually, I own an '07 Ultra and it is the best bike I've ever owned. It's comfortable for longer rides and still a lot of fun in the twisties. I have mine setup more like your SG though as my wife no longer rides so I pretty much ride without the Tourpak and with a solo seat and short windscreen.
There are a few mechanical issues that you will read about from time to time. Cam and primary chain tensioners wearing prematurely. Inner primary bearing failure, compensator problems and of course many will tell you your tranny will fail, it's just a matter of time.
I've got about 58,000 miles on mine and I've not had any of the problems mentioned however and I think with proper maintenance you should get many trouble free miles.
I have upgraded my motor to a stage 2 which includes a Screamin' Eagle Intake, True Dual Headers with Rinehart Slip-ons. S&S Easy Start Cams (which will, IMHO help avoid the previously mentioned compensator failure), S&S Adjustable Push Rods and new Fueling Reaper Lifters. My bike now has plenty of power and enough so that I don't feel the need for any future motor work. I have upgraded the clutch to a Barnett Kevlar (required after the cam upgrade as stock clutch wouldn't hook up well with the added power) and I've also changed out the inner primary with a Baker IPB, as I was in there already to fix a leaking shift shaft seal.
One other thing, if you do any upgrades and need fuel management I would highly recommend the Power Vision tuner. After going in circles with the PCV, Autotune Unit and even spending wasting $400 on a dyno tune, the best money I spent was with Fuel Moto on the Power Vision.
Now post some pictures of your new ride and get out there and put some miles on that thing.
This is the first year of the hydraulic cam followers, so that problem is almost...not quite moot. Like Danzio says, be careful about jumping in too soon with additions to the bike...you can easily be spending money on things that really don't matter, OR on things that actually aren't as good as other things you could be spending better money on. The Fuel Moto Power Vision is one good example. See how the power that the bike has now works for you...unless your interest is in burning tires off the rear wheel...like why would you buy a touring bike for that but some guys do and smile all the way to the tire store...then be judicious with power modifications. I just came off of a 2006 Street Glide, and with the 88 CI engine, Stage One...it had plenty of power for two up riding...I go 250, wife goes 140 or so...never a problem with any of the terrain in SoCal, or with riding with other guys.
So, with your 96 CI engine and six speed, you should be set. Yours has the older frame, and as the years go on, you'll find aftermarket parts getting a little harder to find, but right now, all is well. If your focus is you, the bike, and the road, it will work just as well as a brand new bike for ya!
I've got an 07 Ultra Classic. It's been a great bike for me but the P.O. suffered a catastrophic engine failure when the pressed crank spun. Fortunately he had the ESP on it and I got a bike with 2000 miles (20k overall) on an engine with a welded and trued crank and stage two upgrades.
I don't mean for that to worry you but that could be a concern for that engine.
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