Well, far be it from me to swim against this riptide! :-) I've ordered another crosshead/pilaster set. metromom, the crosshead and pilasters are Fypon millwork (bought from accentbuildingproducts.com) and the wainscoting was DIY with pocket-screwed MDF and cove molding (photo of WIP below). Given the product size offerings and dimensional needs/limitations, I can't make the door surround much bigger, but I did buy a keystone to go in the middle of the door crosshead to dress it up a bit.

I live in a 70+ year old Cape. This door had always been painted to match the trim. This year, I decided to strip it and stain it. Here are the results. Since all the trim in my house is painted an 'almost white', I wouldn't consider stripping the surrounding trim.

I vote for painting the sidelights on your home. The photos above are lovely but I think those work because of the amount of decorative molding that is around each door. You don't have much headroom above your door and I'd paint the sidelights to add more weight to your door area. If you want to get carried away with remodeling, look into redesigning the molding above your entry. ;) The example below is of DS's house before fixtures were replaced. Here is a link that might be useful:

All the same color because it's essentially one in the same element. In other words, you can have a door with no side lights but you can't have side lights without a door. That's why it doesn't make sense to paint the side lights a different color from the door.