Using conditional tags to control Output and Dynamic Content Filtering

I am trying to set up a project with two outputs, one to a Microsoft CHM and one to HTML5. I want a different stylesheet used in each case so I have used a conditional tag to link to the css for each output. This works well.

The site documents software features and I now want to add a dynamic content filter that will change visibility of the pages according to a condition tag (I have tags for 2024 and 2025 currently).

I built a test project with four pages. I applied a 2024 tag to one page, a 2025 tag to another page, and no tag to the others. Dynamic filtering worked well.

When I add in the output condition it fails. If I have the output condition and I add the year filtering, it fails. Ii seems you can use the date condition tag OR the output condition tag. 

Is there a way to combine them to produce a web outout that has the date filtering capability, and a chm that also allows date filtering?