1 pointThat must be a Skycut 60" https://www.sky-cut.com/page89?product_id=76 Those cutters are sold here as the Prism Cut in 20" and 28".
1 pointI am still running my Flexistarter 8.6 on XP, and never have problems. Have you tried to reinstall your Flexistarter? Do a system restore on your computer. Turn off the updates on your computer.
1 pointI think you answered your own question, a windows update happened. Find you an older, offline PC and run WindowsXP and forget about updates.