Hate to plug for a tool, but have to do it here.
I wouldn't create something like this from scratch if I could spend a few hundred bucks on 3rd party controls.
See this for some inspiration:
https://demos.devexpress.com/ASPxGridViewDemos/Templates/CardView.aspx[
^]
I'm sure it can be done with the built in grid view - but it may take extending the default .NET grid view control significantly to make it all work right. A clever 3rd party control like I've shown a demo for above would make this into a trivial matter...and look way better than the .NET default grid.
If spending $ is not realistic, perhaps you can do something else with the grid view or use a different control (since you are essentially creating something like a "card view"). Something like the list view control allows for full template customization - so you can make things look however you like.