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 and I can see that there is a nugget entirely devoted to row-based transactions vs. set-based transactions, so I'm confident I'll shortly have a better understanding of how a T-SQL programmer needs to think relative to relative to relational databases (and set theory, at a higher level).

For a better understanding of what I've been trying to accomplish, I'll post some results below:

Re: The ChestItems table, It's purpose is to be a one-to-many join table between Chests and Items. A chest can have many Items, but an Item can have one Chest:

ChestItemsID ChestID ItemID

------------ ----------- -----------

1 1 60002

2 1 60014

3 1 60015

4 1 60021

5 1 60031

6 1 60038

7 2 60004

8 2 60007

9 2 60012

10 2 60019

The purpose of the WHILE loop around the INSERT was to ensure that I was putting x Items into the same chest. If there is a better method of implementation, please share it with me. I am humbled by the help I've already received and appreciate any more that comes my way.