@glued2thefloor, unrelated to your problem, but you may be interested in the 'Percent string literals` https://crystal-lang.org/reference/syntax_and_semantics/literals/string.html that would allow you to not have to escape quotes:
things = "cats"
"\"#{things}\"" == %<"#{things}">
https://play.crystal-lang.org/#/r/95hj
Also, I believe system command automatically inherits stderr and stdout from your current process.
https://crystal-lang.org/api/0.34.0/toplevel.html#system(command:String,args=nil):Bool-class-method