Thanks Jeff for the detailed insight on the necessary shift in programmatic perspective, I truly appreciate the help!

Right now I'm taking the training courses offered through CBT Nuggets on 70-461...

Thanks everybody for the help! Here is what I ended up with:

USE DiabloLootSystemClone

Go

DECLARE @counter int

SET @counter = 1

WHILE @counter <= 1000

BEGIN

INSERT ChestItems

SELECT c.ChestID

,i.ItemID

FROM Chests...

Thanks everyone for the quick responses and the helpful attitude! I come from a C# programming background where iterative loops aren't as costly, So i'll definitely be reading that article!...