Hi Mike
"I have the option to match on post date but not current date."
When you add query filters to a View you are comparing against something.
So when using post date, for example, you can set up the View that queries the database for posts to say "only return posts whose post_date is later than 1 Jan 2018" which would only retrieve posts published this year. Bringing "today" into the mix, you could say "only return posts whose post_date is later than today" which would retrieve posts that are scheduled for publication but not yet published.
"Today" is being compared against the "post_date" field value of each possibly matching post.
It seems like you are describing something very different.
"If today is a day in December then show posts with the 'Christmas' category", or something similar.
In which case, we are really talking about optionally applying a taxonomy filter depending on some particular date-related condition.
That's not something you can set up in the GUI, you would need to write some custom PHP for that, where you use the wpv_filter_query API hook to trigger code that checks the current date and infers what taxonomy term to filter by.
The simplest version would be a series of if-then statements (if today is mid- to end-October then show posts with the "Halloween" category, if today is December, Christmas etc.).
If you wanted to get a little more sophisticated you could add term meta for the applicable dates to each seasonal category and add new ones in the WP backend, including the dates, and have it applied entirely automatically.
That implies more complex code, and I'm not sure what you are comfortable with. I can't write the code for you, but if you try and get stuck I will be happy to help, or you could recruit a Toolset Contractor to do it for you: toolset.com/contractors/
https://toolset.com/documentation/programmer-reference/views-filters/#wpv_filter_query
