A little basic Photoshop education needed.

[Denis Kolar]

In PS, when you have something selected, clicking Command/J will copy it in the new layer.
Or grab the layer in the Layers palette and drag it on top of the "New Layer" icon and release, that will make the duplicate layer.
Ater you do it 5 times, just spread all 5 of them on the 11x17 document.

[IntegrityShirts]

Yet another easy way I duplicate layers in PS in windows is just by holding down CTRL + ALT while clicking on the art.  Once you click down on the mouse add in the shift button to restrict movement to vertical. horizontal or diagonal.

To type in a perfect circle in illustrator, shift drag an ellipse, then hold down on the T text tool until the pop out comes on and choose "type on a path" option.  That will get your text on the OUTSIDE of the path.  Then you can go under menus Type/Type On A Path/Type On A Path Options which opens up some other options for text alignment along that given shape.