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>I find myself more often just biting the bullet and re-buying some old classics when they get "Enhanced" editions

People have to do real work to produce newer versions of software, often this work is quite extensive (newer graphics APIs, resolutions, art assets, etc.) If it wasn't a viable enterprise this work wouldn't get done. It's not reasonable to expect perpetual free upgrades.



It still does get done, in many ways, by the fan community. Commercial entities updating games en masse as it is happening now is fairly new.




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