C150? Old ones do the job as cheap as chips trainers, but they will never be an aeroplane.
Yeah, I think 150's are actually airplanes.
I'm sure a Chipmunk is a true delight to fly, those I trust tell me so. If the budget permits, and the role is filled, buy Chipmunk by all means! I don't know what it costs to operate one, though I've been hired to make some special tools, and modify pistions to simply enable the rebuild of the engines. I have participated in a Gypsy rebuild, and conducted field repairs. I'm sure that there are type clubs and support groups to keep a Chipmunk happily airborne, and that is as it should be. They must have set prices to remain profitable, as any business must be to survive. My appreciation to those who will bear the expense to keep worthy older aircraft in service.
But understand why you're considering the Chipmunk - Nice to fly, iconic, and able to be fitted with a nice looking canopy if you wish
. But you're
not buying one if you simply want to be airborne with predictable economy, and lesser expectation of feeling the sky - there are more than 100,000 boring, lack-lustre handling American spam cans out there for that! Great sales for a reason, longevity because of simple economy of scale.
My other flying aircraft is a type certified model, of which only 38 were ever made, and only six survive (though I also own a second, which will be the seventh flying in the world this summer). Mine also has a one off, totally unique engine installation, which is flawed, so I know a thing or two about owning an unusual, and hard to support aircraft. And it has terrible handling compared to my 150!
Simply understand the realistic operating cost of the aircraft you want to own, and assure you have decent contingency fund for it beyond that. It's not the plane's fault if it's expensive to maintain compared to the economy models in which nearly all of us learned to fly.
To be objective, I've never flown the DHC-1 (though would delight for the opportunity), but have owned a 150 for 29 years.....