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If you are going to buy an 88 and put a "big bore" 95 kit on it, why not just get a 96 and put the same "big bore" kit but have a 103? No comparison. The 96 with the \\;SAME mods as an 88 will have more power.
Both are great engines. I now have an 07 Rk Classic, runs hotter then the 88 inch. After 07 there is a cat convert added. This has to change power some. Also, the six speed is a nics tranny. HD touring, 07 and later.
If you are asking which year, I would suggest an 07. It has 96/6 speed and none of the throttle by wire crap. New style oil pump and cam chains. With the basics,air filter,mufflers,fuel management and different cams, about 90 hp. and 95 tq.
I had before and after dyno runs done on my 08 Ultra last fall when I had the stage-1 done. The pure stock 96 came in just slightly ahead of a pure stock 88, less than 5 hp and 5 fp torque higher. So there is not a lot of difference, but the 96 is a little stronger.
When I first rode an '07 RK demo in Aug. '06 I was immediately impressed with the new motor, even stone stock with only 50 miles on the clock. What was most apparent was the improved low-end, which is a meaningful improvement. This planted a seed in my head and within three months I had a new SG after owning a '96 RK for nine years. My friends thought I would never get rid of that bike.
Stories of a TC88 staying "dead even" with a similar TC96 isn't surprising, because the TC96 produces little more HP. The difference is the TQ, and more importantly where it is in the RPM range, which is much better on the TC96 in the low-end and midrange. \\; A good example of this is here:
Scroll down to the dyno charts. \\; Notice that a TC96 RK produces 10 ft/lbs more TQ and 3 more HP than a 2004 TC88 "touring model" with the same equipment. The HP difference won't make you blow past your buddies on TC88's when in an all-out drag race with RPM's at their max, but ask them to crack you from 50mph in 5th gear. That's the practical difference giving you the power where you need it to pass trucks, etc.
If you are asking which year, I would suggest an 07. It has 96/6 speed and none of the throttle by wire crap. New style oil pump and cam chains. With the basics,air filter,mufflers,fuel management and different cams, about 90 hp. and 95 tq.
The '07 is fine if it is equipped with IDS (cush drive), which is standard on '08's. You make a good point about the tensioner issue, which is a big advantage for the TC96 unless you want to fork over the bucks to upgrade a TC88 to TC96-style chains and tensioners (e.g., Andrews) or gear drive.
If you don't do this you're resigned to tensioner checks every 20k or so. The 95 TQ figure is about the max you can achieve with a stock TC96, but I've never seen one even come close to 90HP. The Fuel Moto setup is about as high as it goes, and Jamie has gotten his RK up to about 80HP. The key is the TQ, which on his test bike is 94 from about 3000-3700rpm.
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