My two oldest cameras are:
A chrome Leica M2 with Elmar 2,8/50, bought second hand. I saved money from selling newspapers on sunday mornings as a young school-boy and bought it in 1969. My school teacher sold his camera to me for 900 Skr, about 90 $.
Rolleiflex Tessar 3,5/75 which I bought earlier in 1968 in a Photo store för 375 Skr, about 37,5 $.
Of these two I have used the Leica most, I bought a new black Summicron 2/35 after two or three years and also a new Elmar 2,8/90 some time later.
I still own both cameras now after 50 years (yes, I am old and I will soon retire!) and use them a couple of times each year. They still work fine. But now when I am older I can afford more cameras and lenses. I have bought some of my old dream cameras in the last years. I now have among others a M3, M4P, M6, M9 and M (240). Of these I like best the M2 and the M6, but the M9 is also a nice camera if you want digital images!