I don't seem to have a huge problem reading early American handwriting, and I always figured it was because I have taught public school, where you really have to be able to read and decipher all manner of strange permutations in writing.
I was at the family history library last week, and the man at the microfilm reader next to me asked if I could tell what some writing on his screen said. It was very clear to me, so I told him, and he thanked me. Later, he asked me for help again, and it was the exact same name in the exact same handwriting, which surprised me.
After helping him again, I commented that maybe it was easier for me because I've taught school. I then joked about how only pharmacists may be better at deciphering handwriting than school teachers. He asked me if I knew any pharmacists, and it occurred to me that he might be one. It turns out that he was, and he said pharmacists only have to decipher specific Latin abbreviations in doctors' prescriptions--there are only a few things the handwriting might say. Not so with early American handwriting, apparently.