W10 Ver 1903
On occasion, all my chrome tiles will disappear from my Start Menu...usually following a W10 update.
It's very frustrating. I've stopped trying to customize my start menu directly with Chrome shortcuts.
My solution is to use standard Windows folders to hold my Chrome shortcuts...and pin those folders to the start menu.
Windows will not disturb the folders.
I have a "Chrome Apps" folder which contains shortcuts for some standard Chrome Apps.
I have a "Chrome Shortcuts" folder for favorite Chrome shortcuts to my personal web sites.
I have other "custom folders" for groups of specific shortcuts organized using Start Menu Groups.
I create my shortcuts by going to "chrome://apps/" and using "right click/create shortcuts" to be placed into my folders.