That sure looks like an elementary classroom behind your bike!

I did most of my trips in my younger days with a ground cloth and a tarp. I only put up the tarp if there was a chance of rain. It saved quite a bit of space, but wasn't fun when mosquitoes were bad.

I had a issue similar to yours with the angle of my front rack on my 30 year old mountain bike. I ended up extending the lower mounts out by adding a short length of metal.