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I installed the HD last year by myself. I used one of hte writeups I found on CF. I took my time and cleaned under the fenderwells, A-arms and the backs of my rims and I spent about 4 hours. If you do the shocks only I would say figure 2.5 to 3 hours. I had a hard time compressing the upper rubber bushings enough to hand tighten the top nuts on the front shocks. I think I used the olds one on one side since they were compressed more and I was tired of playing with them. I would do the fronts first since they took longer and maybe you wont loose your patients. Have fun!
I am getting ready to change out the shocks in my 2001 for Bilstien HDs...
Anything tricky I should be watching for?
About how long should it take?
Will I need a lift or is a floor jack sufficient?
Yes it can be tricky. When you're doing the rears, make SURE you don't tear the axle boots. I tore my driver's side trying to get the spring out.
To avoid this, just compress the spring AND tie it up with a couple large zip ties for BOTH removal and installation. If you do this, the job will be much, much easier.
It took me a few hours, I can't say for sure since I did sway bars at the same time. However, I didn't zip tie the old shocks coming off and it made the removal much more difficult than it needed to be.
You can use a floor jack if you have one that will lift the car high enough to get the wheel off.