Do I really need to change transmission filter/fluid? and for how much $$$$?

The first guy said the fluid was black but you need to verify this. If the fluid is really black in color then maybe you need to hold off on any transmission servicing.
Black fluid means the transmission is going out and this dark color is due to friction material, overheated fluid, etc.
In other words, start planning for a new transmission or car if this is the case.