I have a set of stretched bags from a '14 CVO RK I'd like to have painted for my '17 Laguna Orange RGS. Would it be possible or am I better off trying to sell these and using the $$ to buy from HD?

 

I think you can get them painted for a lot less than buying ones from HD. If you needed a CVO color, that is another story. There are few people that can match the CVO colors.
However, you can post these for sale in the Touring Parts section and see how much you can get. There might be someone who dropped or scrapped their bags and want to purchase already painted.

 

Yes, the CVO color match is a huge pain in the butt... It can be done, but have some patients because it will take some trial and error. I say this from experience. But other than that, scratch, smooth, seal, and go. Either use the paint code from your bike (if it is not a cvo color because HD keeps a lid on that stuff) or if your current paint is a few years old go somewhere like Automotive Paint Supply and let them scan and match. May not be perfect, but will be really close. The scan can help match after a bit of sun fade. Pay attention to what clear coat you use. That can change the paint tint a bit as some have a slight yellowish tint to them, so don't skimp on that.

 

PPG produces Laguna Orange paint for Harley. Try seeing how much it cost at you local PPG jobber.