I finally finished dressing the loom! I even used the warping board to get there.
The folks on the Beginner Weaving group on Ravelry were a great deal of help and encouragement. It turns out that I wound the loom incorrectly, put too much yarn on the warping board, and did not tie the warp tightly enough before I removed it from the board. I still think I could do better, but it was still better than the last try.
My friend the art teacher and little Grump also helped me keep everything straight before I threaded the warp onto the heddle. It would have been a mess without them.
Tomorrow, I might actually get to weave!