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I ahve not done it but have read about many people that have. I am sure it can be done at home as long as you are not all thumbs. You might want to contact DAWG or PhilM as they have done everything at least once. I can't pony up the cash for that tranny right now or I'd do it too.
If you are reasonably competent working on stuff (which you must be since you are asking), it've not a big deal as long as ya have the necessary tools.
You can get the tools ya need from GeorgesGrarge.com for a decent price, but you're probably still looking at close to $400 in specialty tools.
The process is reasonably simple & straight forward.
On a scale of 1 ~ 10.... I'd say 7.5 the first time, then 5 after you've done it.
One thought... there is a guy on HTT that rents a lot of tools, but I'm not sure if I've seen tranny stuff there or not.
You WILL need a standard issue HD service manual for your particular bike.
the specific tools you will need to do this will be to pull the bushing off the mainshaft outside of the final pulley, an extended deep socket to remove the final pully and a press to remove the mainshaft and counter shaft from the face plate of the tranny. You will probably have to do a little grinding inside the tranny case for the extra gears to fit. That's something you will have to play by ear.
PhilM is dead on the price of tools and benefits from adding a 6 speed. For others thinking about doing the same you may want to consider other options... The older (1999 vintage) twin cam fuel injection bikes had the 3:37 final ratio. And many have converted the newer bikes to the 3.37. If you are one of them then I'd suggest you look at a true overdrive gearset (.86 OD). Both Baker and Jim's make them. (the Jim's is a lawful copy of the Baker).
Something else ya have to consider with the DD6. It was designed for racing, upshifting fast. Down shifting is another story. If ya downshift in the typical, easy kind of fashion, you will get gear grinding. Ya have to do it with a solid shift, each gear.
Check my garage photos to see where I had to grind the tranny case inside for the gears to fit properly. Yours may or may not have to be ground, only way to find out is to give it a shot. And no, all those 'specialty' tools are NOT necessary. If it gives you pleasure to spend the cash so you can show your friends what expensive tools you have for a one time use job, go for it. I have posted on the Triked, hacked, and trailering section, and a few other places, detailed info on how I did mine without them. As was said earlier, the first time is the hardest. After you have done it once you will need those specialty tools even less.
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