The average consumer would be much more attracted to an ad showing a bare bones bike with lots of extras laying around it than they would the fully dressed bike alone....but I like jbl's suggestion....sell the bare bike then ebay the goodies.

 

+1 on the photo hosting service and the bigger pics. Those crummy little Craigslist photos don't sell anything.

 

You are selling a Heritage not a Fatboy or Deluxe, so use a full dress picture for the primary and a stripped picture as an extra. Looks like you posted before and after pics, so take new ones so the bike matches in all the shots and looks as it is today. When you take new pictures of the bike, don't put your helmet on handlebars. If you are also including a lot of parts or clothing, organize them on a clean surface and include a pic of them as well.

 

If you have all the stock stuff i would sell it as stock and sell all the extra stuff seperately...you will make a lot more money.