Small Jobs - Wedding/Anniversary Portraits: How do you differentiate between the various types of artwork you do?

I've always made artwork for friends and family. Last summer was my parents' 25th anniversary and I made them a painting as a surprise. I also attended one of my friend's weddings and painted a portrait, and this summer I will be going to another friend's wedding - I'm in the middle of painting their portrait. I've never charged for any of these paintings, I mainly give them as gifts but I've been thinking of possible small jobs to supplement my income lately and this seems like a viable option. The Reno community is great at supporting local artists and I've already looked into a couple vendor opportunities. In our BFA/MFA Intermedia course we've been discussing the role of the artist outside of the studio and academia, specifically how to be an artist and the different ways you can approach being an artist in the real world. In thinking about these wedding/anniversary portraits I can't help but think about who my audience is, it's obviously not a gallery or the museum - it would be the average person. Does that mean I'll be compared to the business practices of Thomas Kinkade (on a much smaller scale)? If I pursue this, how do I find the line between commercial paintings and paintings that are more for 'fine art' settings?