As the title states, I am trying to count across cell ranges on a separate sheet but cant seem to get it to work. Any help would be greatly appreciated.
=COUNTIF
You cannot use the MONTH function as a form of sub-function in a COUNTIFS function. You need to add an extra level of calculation with something like a SUMPRODUCT function.
=SUMPRODUCT((MONTH(original!A2:A58)=1)*(original!D2:D58="East"))
That should count the instances where the month of the date in the Original worksheet's column A is January and the corresponding row's column D is East.
If you prefer to stay with a COUNTIFS and can keep the dates to a single year, you can provide a start date and end date which will bracket the month of January for a particular year.
=COUNTIFS(Original!A2:A58,">="&DATE(2015,1,1),Original!A2:A58,"<"&DATE(2015,2,1),Original!D2:D58,"East")
The default comparison operator for COUNTIFS is equals. There is no need to type it in.