Couldn't help but jump in here. I have been blessed to have owned and flown 33 airplanes over the last 32 years from an Alon Aircoup to a Cessna 421. Currently have 7 different airplanes that serve different purposes.
My RV9 that I purchased recently serves to fly formation at Spruce Creek, 7FL6. The other aircraft I just can't bring myself to sell are:
1929 Waco CSO open cockpit 3 passenger - to give rides of course.
1939 Waco Custom Cabin - to take all the camp gear and numerous grand kids to Oshkosh,
1946 Piper J3 - the best Young Eagle airplane around, pure flying.
1955 Piper Pacer - first restoration and went way overboard with Garmin 430 panel and took runner up in class at Oshkosh 2006. This one will get passed down to my aviation oriented grandson.
1956 G35 Bonanza - retract and high performance time builder for key employees, friends and family.
1984 Bonanza A36 - traveling machine that hauls everything on one engine.
Now if I had to get down to two I would sell

???? nope, just can't do it.