Softtail or Dyna?,its easy .You will need a lift..There are many choices.You can go with lowered shocks or extensions that bolt directly on to existing shocks but beware,your ride will suffer if you use these as well as the passengers. Best go with new shocks.HD carries them as well as JP Cycles.If its a Dyna pr Sportster, there are brackets available that go on the bottom of the shocks.,There are also considerations withe these also ,but the cheapest way. There is a co.In Waco Tx that sells brackets that will lower it 2".Most only 1 " .Again,to lower its best to go with lowering shocks..Both types are very easy to install. Do a Google search and you will find an abundance of choices.
I've got the shocks on my 06' Standard. The ride is i little stiffer, but hey I can reach the ground now. Simple install. I have the front lowering kit, but will have the dealer do that.
I have heard about the rear tire bottoming out on speed bumps and whatnot... What about the pegs? Any problems with clearance there? That is my biggest concern when thinking about lowering the bike.
I lowered the front of my Deluxe and it scrape under the footboard and mustache engine guard during tight cornering. I'm planning to lower the rear for about an inch; but I'm still deciding weither to do it or not.