I also generally change oil and filter once a year. I have only put 2500 miles on my VRSCR so far this year, so I will likely stick with conventional oil and save over half the cost of oil compared to synthetic (5 quarts for this bike). However, if I had ridden 5000 miles over the summer, I would change to synthetic, but still change it once a year. When it comes to oil and change intervals, you are going find that opinions vary greatly (just like politics), the key word here being OPINION. If in doubt, stick with the HD recommendations for change intervals, and you won't have any issues.
Usually oil manufacturers will recommend change intervals for their specific oils. I will give an example: I had a KX125 two stroke dirt bike that required a 32:1 mix. However using Amsoil synthetic two stroke oil allows you to mix 50:1 without any ill effects. I sent an email to them to confirm it for the KX application, and they replied within a day or so to ensure me that mixing 50:1 was no problem.