Using the cordless and a pencil was pretty smart and a lot faster than doing it by hand the entire time. Yes, the crinkling sucked, but I don't know what could have been done about it. It's not like you can iron the tape.
That is a really good idea, I wish I would've thought of that back then. Once in a while I could decently rethread a tape by hand, but usually I would just give up. I never knew anyone who could consistently fix a tape, it was just one of the irritating things about cassettes.