If it were my car I'd wear out all of the 14" tires and have the 15" Rally II wheels painted and ready and put them on when it's time for new tires.
Personally I only like using 14" wheels on the older cars to get a factory look with either plain blackwalls, thin whitewalls or redline tires in 70 or 75-series sizes. I'll be running a set of 14x6" plain steel wheels with either stock '64 spinner hubcaps or poverty caps on my '64 LeMans convertible, I have a set of 215/70-14 whitewalls I will use for a while.
For a more performance-oriented car I like using 15" wheels and 60-series tires.
It's all personal preference and keeping with the theme of the car and the purpose it's built for. I have some '64 Pontiac A-body cars set up with 17" and 18" wheels too (defintely performance-oriented).
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