I currently have a bunch of speculative $100 to $200 tickets that I may cancel at some point and a few $100 to $200 flight credits from past canceled flights and $500 in a southwest gift card.

I'm a little confused by your advice.

What's wrong with just keeping multiple smaller amounts around?

If I were to have ten $100 credits and book a $150 WGA flight after the changes. Then I'm left with eight $100 non credits and a $50 flight credit. Still non expiring.

And if I cancel that flight then I'd have $150 that I'd have to use in the next six months.

How would consolidating flight credits help me?