I have a few games installed through Itch.io for awhile now.
I launch a specific game, get a popup to chose version. There are 25 versions installed. They're all the same name (name of game), no other data included (version number, install date). They're not organised (last version installed can be anywhere in the list) and it's incredibly annoying to have to check which is the latest version of the game in the game description, then having to launch the game between 1 and 25 times just to potentially find which is the latest.
For small games, it's easier since even the smallest changes will be visible in the only meta-data displayed on the popup (size of version) but if you have larger games, the size difference between versions is not always displayed. In my earlier example, I have 10/25 versions with identical size 250KiB with the others being smaller. So unless the new version isn't extra content but cleaning up of the game code for efficiency, the larger file will most likely be the correct one.
To the DEVs who work for Itch.io : Please, this shouldn't be a difficult change to implement but either make the list of installed versions ordered on release date or installation date or have it display the version number.