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It is unclear exactly how your lookup table is structured - appears to have 4 sets of 4 columns, but all the data should be in 4 columns only.
The easiest way to get your desired price is to use SUMIFS. BUT, and this is a big requirement, your entries in the dropdowns need to exactly match the values in your lookup table. For example, in your top table, you have two cells:
| Extension Ladder | 24 Ft. |
|---|
In the bottom table, you have "24 Ft. Ext Ladder" The top table should also have "24 Ft. Ext Ladder" as the entry. Or your lookup table needs to have the entries split across two columns as well.
Anyway, to return the price, you could use SUMIFS like
=SUMIFS(price column, description column, description, duration column, unit of duration)