You should be able to use a lookup function for this.

First, you need to get all of your descriptions matched up. You can't
do a lookup unless terms match. You want to use the "3" under Contract
Term to match the column headers on Sheet 2. And you want the "One-
Sixth Square" to match to the row headers on Sheet 2. It looks like
the row headers match fine, but you need to find a way to make the "3"
match to something. It can either be used to simply number the columns
(as you suggested), or it can match directly to the words at top,
which are currently "3 mo. Rate". And then this needs to work for all
your possible choices, 3 month, 6 month, etc.

If the above are your actual column/row labels, it should be ok. You
might put in column E:
=VLOOKUP(D2,Sheet2!A1:H100,MATCH(B2&" mo. Rate Commission",Sheet2!
A1:H1,0),FALSE)