It looks like I'll be sailing in Catalina 27's and 250's for the next
year.

I've been reading a lot about:
Tiny boat: Take every wind shift.
Huge boat: Not always! With the time/distance lost in turning a large
boat this may not be best.

So what would be the general rule for 25-27 footers?

What rules/guidelines do I use to learn properly the best way or
frequency or wind shift arc to tack?