Any good rider should know how to change their oil. Basic maintenance that you can do at home saves you money in the long run and really lets you feel more involved with your motorcycle. It may even be the kick in the pants you need to dip your toes into the bolt-on customization side of the pool. Which may in turn lead you to actually making your own parts for it someday.
S&S Cycle knows more about V-twin motors than just about anyone else in the entire industry. They should; the company's been in business since the time of the production Panhead. Here's a video clip for you of their insights on dealing with oil filters.