> It's more complicated than that since the cost of housing is included in "official" and unofficial inflation numbers (33% of US Consumer Price Index is housing).
No, the costs of homes-as-assets is not included in CPI (the cost of housing-as-a-consumed-service, rent, either as paid by renters or as foregone by resident homeowners, is.)
> So multiplying by the inflation rate and comparing to the current market is circular.
No, even if it was a CPI component (as all consumer goods are), it would still be correct to use the whole CPI to get its inflation adjusted price.
> A better indicator might be the inflation in the money supply over that same period
No, while money supply changes have an effect on consumer prices, if you are looking for a price deflator for purchasing power equivalence, the CPI or other broad price index (PCE, etc.) is a much better choice, even for consumer goods that will be components of the index.