What issues are you getting with the cascading filter for option 2?
You could use a Rows layout and stack sections on top of each other – for the title + tooltip, set the section layout to Toolbar and the + signs where you can add widgets will be on the sides. You could then use the Markdown widget for the label and a button group with no label (just the info tooltip icon) and a description so when a user hovers their cursor over it, they can see the desired text.
Another thing you can maybe play around with is the alternative display option for filter lists which will make each property (i.e., Payer) look like a pill/rectangle with rounded corners. You might use one filter list widget for each property (not ideal) but then can arrange them in a columns layout where there’s a button group widget (same implementation as described above) and customize the space between each filter list + button group pair.