I own my Citabria ('65 7ECA with O-200), and it makes absolutely zero financial sense.
I fly between 50-75 hours per year, and my direct costs are pretty small – under $30 per hour for gas, oil, and filters for 2 oil changes (my labor). Flying 50 hours a year, insurance adds $12.40 / hour, and an annual inspection adds about $15 / hour. Still, at roughly $60 per hour, those direct costs are WAY cheaper than anything I can rent around here (where 172s with instructors go for $275/hr at the local flight school).
But the killer expense here on the east side of the DFW metroplex is hangar rental ($345/month), which quadruples my costs, adding $82.80 per hour! And that's sharing a hanger (and splitting costs 50/50) with another guy. Suddenly I'm at almost $145 per hour – a number that seems totally ridiculous for a 85-90 mph cruise 2-seater!
But I don't regret any of it. I never have to worry about going to the airport, only to find someone didn't return on time so my flight has to be scrubbed. I never find any trash in my airplane, or that someone left the master switch on and the battery is dead. I never have scheduling conflicts when I decide on Saturday morning that I'm going to fly to Austin to see my grandkids for a couple of hours. If I want to make a sunrise or sunset flight at the last minute, I just jump in the car and go, with no worries about whether the plane is available or not.
Scratching that tail-dragger itch is what it's all about. And to me, it's worth every penny! After all, if I wasn't spending it on aviation-related stuff, I'd probably just waste it!