I don't know about the first half of those 50 years, but over the second half (2001-today), transportation - or at least cars - got significantly more expensive. Disappearance of cheap new cars + massive supply reduction of used cars + repair costs of old cars + gas prices.
Inflation has been high enough that it messes with our perception of things, but I believe the data shows otherwise (at least in the US).
- Disappearance of cheap new cars: You can get entry level Chevys, Kias, and Hyundais for < $25k, which is about $14k in 2001 dollars and many more of those cars will last until 200,000 miles and have safety features only available on luxury cars in 2001.
- Massive supply reduction of used cars: I actually don't have good data on this, but it seems like there's pipeline is still borked from COVID era irregularities. That said, cars these days have much better quality and last longer. A car with more than 100,000 miles in the 90s was near the end of its life. That's a typical listing Facebook marketplace these days.
- Repair costs of old cars: Repairs can be expensive, but again, cars today are much more reliable than they were in the 90s or earlier. Even simple things like recommended oil change frequency changing from 3k miles to 10k miles for most models makes a huge difference in total cost of ownership.
- Gas prices: Gas prices have certainly spiked recently (gee, I wonder why), but the cost of gas in real dollars has been higher several times in the past 25 years (see the second chart here: https://www.macrotrends.net/4453/us-gasoline-prices) It peaked in 2008 over $6 per gallon in 2026 dollars.