If you have to do stupid tricks such as concatenate statements with ; and create long lines, it's not a useful trick.
In general, reading even the original code, the author doesn't understand Ruby or OO in general. A number of the items would be one-liners with an improved application of theory rather than syntactic rewriting. If the goal is just golfing, then #map and possibly rockets would be better choices.
If I wanted less maintainable code in a shorter line count, I would use a mechanical obfuscator.
In general, reading even the original code, the author doesn't understand Ruby or OO in general. A number of the items would be one-liners with an improved application of theory rather than syntactic rewriting. If the goal is just golfing, then #map and possibly rockets would be better choices.
If I wanted less maintainable code in a shorter line count, I would use a mechanical obfuscator.