I didn't want to post again until I had crossed off at least one thing on my list! So far, I've acquired Yuffie and Vincent and earned the date with Barret, and Aerith has learned all of her Limit Breaks! Earning the date with Barret was easier than I expected it to be. It was everything I hoped for, too (never seen it before tonight)!
I guess I'll attempt to win the Parasol in Speed Square again; then, I think, I'll do the side quest in Wutai. I don't think it's proper to do that particular side quest on disc two. It would be really cruel of Yuffie to steal her comrades' Materia so soon after Aerith was stabbed and killed, don't you think?