I think you should remove a squash and plant it in a whiskey barrel. That would be much less work and since you would only transplant one plant and not several, there is that much less of a risk to damage a plant beyond repair. I have successfully transplanted a squash--they have much fewer roots than you would think and they are definitely easier to transplant than tomatoes (you would most likely lose all your tomato production if you transplanted them now).

Just wanted to add this: you might also want to transplant your pepper plants closer to where you removed the squash from. They are harder to transplant than squash but still much easier than tomatoes. Just make sure you water them thoroughly before you transplant so the soil gets sticky and you can remove the pepper with a large soilball to avoid exposing any roots (which should be about five inches deep and as wide as the plant). If you disturb the roots too much, you might lose your pepper production. Transplant at sundown so any exposed roots have better chances at not drying out before you stick them in their new spots.

Why cant you just trim up the squash plants? Trim off some of those offending leaves. I've done it and had on adverse affect. Just dont trim off the runners.

Viktoria, How deep do the roots go on the squash plants? I'd like an idea of how deep to dig if I moved the plant. Did you see any decrease in the squash production when you moved your plant?

Makete, I've been told differing opinions on trimming squash plants. Some say it's not good to trim off the leaves because they are needed for photosynthesis and also trimming them attracts bugs who eat squash. Others say they've trimmed the leaves and didn't have any issues. I just haven't been sure of what to do. How many leaves did you trim off of yours?
Thank you both!

When I needed to trim my squash plants, I trimmed about 1/5 to 1/4 of the total leaves. I can only give you what I have done, and no adverse effect.