Maybe 2 or 3 times a year, if I’m lucky. Maybe this site will help change that. So far, nope.
The longest paid session I ever had was a 25-hour cuddle session. He is an Orthodox Jew and it was Shabbat. Maybe 4 of those hours we didn't cuddle because we had to eat or bathe (individually, of course).
These days we do minimum 8 hours whenever I see him. He at one point considered bringing me on a business trip to Zurich as his "emotional support human" because traveling outside the country spikes his anxiety and affects his work ability.
Oh, and this was also the week I had scheduled 27 hours of cuddle sessions outside of that. So, yeah. I got paid to cuddle for 52 hours that week and cuddled about 48 of those.
With my primary cuddle buddy, maybe once a month. With my secondary--who may soon be my primary--we've cuddled a couple of times already but once our schedules align this may become more frequent as we both seek frequent cuddles. I've also been considering have a pro be my primary pro that I cuddle with a couple of times a month. The more cuddle buddies I have the more chances I have for cuddling sessions. My ideal cuddling schedule would be bi-weekly. If I have two that I cuddle with bi-weekly, well now I'm getting cuddled once a week on top of any one off sessions I have and my current primary whom I don't always get to cuddle with often.
Most nights my hubby and I cuddle into the couch or the bed with our three kitties and watch Unnus Annus or Markiplier on YouTube. Until the Witcher, Mandelorian or Brooklyn 99 have new stuff lol