Looks like they bought the standalone Office suite, a lifetime license, for about double the price of a year of Office 365. Makes sense if you only need Office on a single PC or Mac (365 can be installed on 5 computers) and store less than 5gb on OneDrive.
1) The author was paying for both Bear and Craft. To me, they serve the same purpose - Markdown notes editors with a sync component. I tried both out (and liked both) but have since settled on Obsidian because I like being able to see my notes as .md files on a device I own.
2) The author mentioned Microsoft Office was a lifetime purchase in 2021 which confused me - are they are referring to Office 2019 instead of Office 365? I don't believe O365 offers a lifetime option.