I have sailed all sorts of rigs in the past - even a junk rig - but have never owned a cutter before - I know each boat is going to handle differently but in general here are the questions:
Manageable breeze - main, headsail and staysail raised
Wind picks up -roll up staysail
more wind - reef main and keep headsail up - maybe rolling in a bit of it
more wind - roll up headsail and roll out staysail
Both headsails are on a furler - main has 3 reef points
Downwind - drop main and have staysail and headsail wing & wing?
Sound about right?
What boat are you talking about ?
Our W28 has a long boom , so when wind picks up we reef the Main (only 2 reef points) and it doesn't have to pick up much like around 18kt . More wind (20-25) , second reef and furl Yankee a bit and reef Staysail .
Down wind for us is a hoot , it doesn't happen enough and it doesn't happen long enough .
Down wind ... Pole out the Yankee to windward , fly the Drifter to Leeward , drop the Staysail and wing the Main to Leeward . Smiles for miles .
It was mentioned that tacking a bigger headsail is a PITA , I would agree with that . Tacking the Drifter one must go forward and the Helmsmand pays attention .
The Drifter is the biggest headsail we have . Back in the day Kern Ferguson was contracted to make sails for Westsail he came up with what he called the Super Yankee , I'm not sure how that one would tack .
This is how our boat works best , when we first got it I sailed it like the Sloop we had prior , big mistake . On the Sloop we would furl the headsail completely , doing that on our Cutter produced a lot of weather helm .