It is not obvious to me what the split criteria is; your regex certainly does not provide the rule since it fails to do what you want. Is the general rule it to split before a decimal, then before decimal again and then before $ ? If not, you need to define the rule.
Also,
testing with a single test case does not allow one to have confidence in the resulting regex.
Edit: Regular expression use "[ just about anything ]" to define a character set so in ("(?=\\b[\\d{1,4}/?-?|\\$\\d{1,3},\\d{1,3}(,\\d{1,3})?]" you have a character set of "[\\d{1,4}/?-?|\\$\\d{1,3},\\d{1,3}(,\\d{1,3})?]" ! Are you expecting the '[' and ']' to in some way group the content?