Boring Variations on a Theme

So....i'm doing more cats erased, in paintings. I'm not sure if i'm going to continue, because i hate repeating myself and i am boring myself to death doing the same painting over again. It's an interesting challenge to make it not boring, and i have to figure out if i am really learning something here.
I'm also working on this painting of a formal wedding portrait, which is maybe one of the ugliest paintings i've ever done, but right now i'm just trying to figure out the idea (if you think you know or are one of the people in the original photo, please don't be alarmed. I tried to change some details to make it more generic looking. Which maybe wrong wrong wrong considering what i say next). The person painted out in this one is a person who is actually close to dying very soon. I keep trying to figure out what is too far, where is that line to cross, for just myself? My next step is to paint over OLD pictures of my family, but that really scares me. First, it feels to historic, like these artifacts are part of my lineage and what i will pass down to future generations. So why do they feel that way and the "contemporary" photos don't? And, that connects to number two in a way...I don't feel like these old photos actually belong to me. They belong to future generations, blah blah, but most of all they belong to my mom. It's HER parents in those photos. That i think is why i feels so wrong, i'm taking something away from her. Thereby, cutting up my own clothes, so to speak. (Maybe that will catch on as a phrase. Probably not)

Update: Here is the painting:




Some questions: Does it matter that the painting is not only not photorealistic, but rather bad and clunky? (I've gotten opinions going both ways - some people like the awkward painting, saying it's charming and sincere). Not sure what i think. I'm still trying to figure out if painting these makes sense. To me it's pushing the believability/trust factor ("Did you really paint the cat??") and also rather than painting out a memory or artifact i'm painting out my own work, my own evidence of labor. How much do you think documentation matters? ie, showing the original painting? The idea of Peformance keeps coming up in my studio too, which i think i mentioned when talking about Janine Antoni. Jon Kessler (who rocks) came to my studio this week and broke it down in a very simple and fertile equation: Verb>Action>Performance. Hmmmm
One more issue that was brought up in Sheila's class (w/ the copies)...Maybe it's not about painting out your real family but painting out your art family. I've been meditating on this for a couple weeks. And it becomes a particularly uneasy situation when placed in the context of Holy SHit, March is Women's History Month. "Kill your heroes" + "Write women back into history". My memory of my grandfather is not nearly as precarious as gender equality. How much does this have to do with the past and how much with the future? Maybe that's enough babbling for now, must get back to work.