I used to avoid "dry clean only" items entirely and only recently started buying them. I realized that I can find better quality jackets and skirts (lined, etc.) if I am willing to buy not only washable clothes. I only have a few things that require dry cleaning (2 jackets, 2 Halogen skirts, some pants).
What are your "mental guidelines" for dry cleaning? I am used to throwing shirts and t-shirts and dresses into the laundry basket after one wearing. I am now cleaning skirts after about 6 uses and do more or less the same with jackets but it sounds like many people don't clean clothes that often.
I am especially curious about what do people do after wearing jackets with sleeveless tops since it seems that collars and underarms would require cleaning after just a few uses.