1. Even though Spenaroo's folks have 5 residential properties as old age financial support, those properties are still available for occupation (rental). They have not contributed to the housing shortage as far as occupancy goes.
2. The purchase price reflects the true current value of a property. The short time on the market is an inducation that the house is not over valued in spite of it being expensive. Simple supply and demand. Capitalism at work.
3. The shortage of sellable houses is a reflection of population growth exceeding house building capacity. Our population growth by 'natural reproduction' is almost nil. Therefore the housing shortage is substantially due to migration, and possibly also foreign investors sitting on unoccupied residential property.
4. It is unrealistic to compare affordability with past history. Because a 'starter home' when I was young, was a simple, compact, 2 bedroom, cottage with no extras. No garage, no driveway or landscaping. The lifestyle of the buyer in 1955 would nowadays be called 'frugal'. No budget allowance for car, or internet, or phone, or takeaway food. And probably located in an outer suburb that had gravel roads, no street lighting, no nearby shopping malls or hospital. All the things that are taken for granted now.
I do not see any entry level homes like this today. Of course current new homes will cost twice (in real terms) what they did when I was young - because they offer twice the lifestyle.