First, sorting is based on field (tag) values in the MC database. It has nothing to do with how the files are organized on disk. You need to have appropriate fields fully populated to effectively sort.
Personally, I would recommend using Categories rather than Panes. Panes are very effective for those you like to do manual selections, whereas Categories allows you to simply browse a view to make your selection. You can try both.
You probably know some of this, but here is some detail on how to do sorting.
You need to create a View that has the appropriate sorting. To customize a view to have the right selection criteria (like Artist is Greatful Dead), right click on an existing view and then select Customize View. From there, choose Select Rules for File Display and add rules that select what should be viewed. In your case, Artist is Greatful Dead should be enough. Add Categories (Field Names) as appropriate to the left hand column.
Once you have selected the view for viewing, go to the top of the view and there will be a small windows with the name of the view. Hover over that and select Sort Options and then Custom. Once in custom you can select the fields you want to sort by in either ascending or descending order. So, sort by Year (ascending), then add Show Date (ascending). A to Z means ascending even it is for numbers like years.
To set the text under each cover, again go to the window at the top of the view and select Thumbnail Text. You can add multiple lines with the appropriate field name. Those will be displayed under each cover.
You will probably have to experiment a little to get it to look like you want it to.