4.) 11points

Lights on -0
Doors closed -3
Windows open -0

Where to Sleep:
Floor -4pt

What to sleep with:
Cover/Quilt - 3pt

Top:
Nothing -0

Bottom:
G-string - 1pt

Rolled an 8 (6+2) aka 38 points! I think I got lucky..

Light off -2
Door closed -3
Bed - 7
Matress - 7
Pillow - 8
Stuffies - 2
Too small shirt - 4
G-string - 1

Roll*
17

sleep with the light off 2 points.

sleep with the door closed 3 points.

sleep with the window closed? 0 points.

12 points left

Floor - 4pt

Cover/Quilt - 3pt

Nipple clamps 1pt

Short shorts - 3pr

I like the look of this. I do have one suggestion, though and that would be to add things that give you points back. Nobody's going to pay to wear nipple clamps all night, but if it gave them the extra point they needed for the mattress, maybe?

You could potentially expand this with vibrators etc.