Toward the end, I'd copy any remaining tasks to a single Toodledo task. I kept the spreadsheet in Microsoft OneDrive, where I could access it from my PC since most of my packing and so on happened at home. I'd filter so that it showed only items that had a y in the Needed column and a blank Done column. After doing a task or packing an item, I'd put a y in the Done column. After I finished, I'd use the filter to show only the tasks/packing items that had a y in the column.
If I needed to do it again this year, I'd type y in the Needed column. For a trip I'd done before (annual business conference), I'd start with what I did the year before and quickly scan the tasks/packing items. I eventually loaded the tasks into Excel, with tasks in rows and trips in two columns: Needed and Done. Talk about different tasks and things to pack!) (One example I remember was a back-to-back business trip at a business-class hotel followed by a camping trip. Interesting! For a while I had travel tasks as separate tasks in Toodledo, but couldn't find an easy way to manage them since, as you noted, the same tasks might not apply to each trip. I have a spreadsheet I set up with travel tasks