That was a fun read. You should do Rails 8.0 on Ruby 1.8 next.
Ruby has had a lot of syntax changes over the years that are incompatible with an older interpreter. An easy example is the 1.9 shorthand hash syntax for symbol keys `{ name: "pants" }` instead of the hashrocket syntax `{ :name => "pants" }`. More recent examples would be keyword args or pattern matching.