Craft Fail? Art Gallery Tote Bag

Well, I'm just not sure that this project worked out.  I had these amateur paintings that I had bought at thrift stores.  I had the idea of making a tote bag out of them.  This is side A:

One side of my Art Gallery Tote Bag turned out fine.

Not too bad.  But this is side B:

The other side, not so much.

There's the problem.  Apparently, the older the canvas, the more likely the paint is to crack and flake off.  Or, perhaps, it was the type of paint.  I'm no expert on these things.  Anyhow, it all happened when I inside-outed the bag at the very end.

Still, I think the idea is a sound one and I'm not giving up on the concept just yet.  In a nutshell, here's what I did.  I started with a thrift store painting that was on a stretched canvas.

I loved this canvas when I saw it at Goodwill.  I thought it would be great on a tote bag.

I pulled the canvas off the stretcher and squared it up, I then sewed it to my tote bag fabric.  I used a plain duck cloth.

At this point, things are still going pretty smoothly.

When you are sewing through this, you want to use an appropriate needle.  I used a Jeans Needle because, essentially, I was sewing through two layers of canvas so I needed something heavy duty.

Use an appropriate needle.

I sewed around the painting using one of the decorative stitches on my machine.  A zigzag stitch would work just as well.

Sewing the canvas to the tote bag fabric.

I do still like the idea of this project so I might give it another chance.  Nothing ventured nothing gained. 

Any ideas what I could do differently to prevent the cracking?