Is the select2 code for generating multiple much different? As soon as I remove multiple, even using jquery 3.4.1 it works.

Yes, Select2 generates an actual placeholder for a single select and uses the placeholder attribute for a multiple select. The reason why it is not visible for a multiple select is because we automatically size the <input> which contains the placeholder attribute.

select2/src/js/select2/selection/search.js

Lines 211 to 225 in 6645ffd

    
           Search.prototype.resizeSearch = function () { 
        
             this.$search.css('width', '25px'); 
        
             var width = ''; 
        
             if (this.$search.attr('placeholder') !== '') { 
        
               width = this.$selection.find('.select2-selection__rendered').innerWidth(); 
        
             } else { 
        
               var minimumWidth = this.$search.val().length + 1; 
        
               width = (minimumWidth * 0.75) + 'em'; 
        
             } 
        
             this.$search.css('width', width); 
        
           };

And for some reason, jQuery 3.3.0 and up is setting it to 0 when the Select2 is not visible.

	Search.prototype.resizeSearch = function () {
	this.$search.css('width', '25px');

	var width = '';

	if (this.$search.attr('placeholder') !== '') {
	width = this.$selection.find('.select2-selection__rendered').innerWidth();
	} else {
	var minimumWidth = this.$search.val().length + 1;

	width = (minimumWidth * 0.75) + 'em';
	}

	this.$search.css('width', width);
	};

Uh oh!

Placeholder not showing #5585

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