Resize then check collide and repeat untill max

Question

I've got a trapezoid that is the guide box and artwork that needs to always be maxed size to fit it.  I've wrote a script that will place the artwork bottom center then move it up 3points so that it isn't touching.  I need the script to loop through and resize by 101% then redo the center function and check collide again.  I'm not even sure if there is a .collide or how to go about that but I went ahead and wrote the rest of the script.  The part that reads "arttouchguide.collide" on line 07 is the part that I'm having problems with and it is just a place holder as I know that it doesn't work right now.  Below the code is a .jpg of what I'm working with.
#target illustrator
  var selecteditem = app.activeDocument.groupItems[0];
  for ( arttouchguide.collide = false)
   selecteditem.resize(101,101);
   centerArt()
function centerArt()
       var thisdoc = app.activeDocument; 
        var selecteditem = app.activeDocument.groupItems[0];
        selecteditem.selected = true;
        var hasDocCoords = app.coordinateSystem == CoordinateSystem.ARTBOARDCOORDINATESYSTEM;
        var p = thisdoc.pageItems; 
        for (var i = 0, l = p.length; i < l; i++) { 
            var pID = p[i]; 
            if (pID.guides == true) { 
                var guideBox = pID 
        var wNum = guideBox.width; 
        var hNum = guideBox.height;
        var swNum = selecteditem.width;
        var shNum = selecteditem.height;
        var sxOffset = (swNum/2);
        var syOffset = (shNum);
        var xOffset = (wNum/2);
        var yOffset = (hNum-3);
        var xNum = guideBox.position[0]+xOffset; 
        var yNum = guideBox.position[1]-yOffset;
        var guideXCenter = xNum-sxOffset;
        var guideYCenter = yNum+(syOffset);
        var sxNum = selecteditem.position[0]+sxOffset;
        var syNum = selecteditem.position[1]-syOffset;
        //to test your script for position un annotate the two alerts below
              // alert("GuideBox Data:\nWidth: "+wNum+"\nHeight: "+hNum+"\nX Position: "+xNum+"\nY Position: "+yNum);
              // alert ("Selected object Data:\nWidth: "+swNum+"\nHeight: "+shNum+"\nX Position: "+sxNum+"\nY Position: "+syNum);
        //changes the position of the selected artwork to the center of the guide box.
        selecteditem.position = [guideXCenter, guideYCenter]   
    }//end centerart
The red line is the guide box, the lime part is the artwork.  It will increase the size of the art, recenter it, move it up 3 points and check for overlap/collide and repeat till it is touching.  This is the only way that I can think of to max out the artwork inside a trapezoid.

Answer 1

I had been working on this since I posted it and between the two posts below I had come up with the following.  Funny thing is one of them is yours Carlos.
How to select only objects within a selection marquee?
Re: How to check if a path fits inside of another path?
There was one more but I failed to bookmark it.  It took the artwork that was selected, rasterized it, live traced it so that you had one path going along the outside of the groupitem.
Here is the code that I have so far;
#target illustrator
  var selecteditem = app.activeDocument.groupItems[0];
  var artworkmax = false
  //to count the number of tries
  var trycount = 0;
if (app.activeDocument.selection.length > 0)
    findguide ()
  if (guidetoggle == false)
      alert ("There is not a guide box to size to")
      }//end if
  for (a=0;artworkmax == false || a>1000; a++)
   selecteditem.resize(102,102);
   centerArt()
   merge()
   findguide()
   trycount++
          if (artworkmax == true)
            alert ("Script tried " + trycount + " number of times")
}/*end if anything open check*/ else
    alert ("Nothing selected")
function centerArt()
       var thisdoc = app.activeDocument; 
        var selecteditem = app.activeDocument.groupItems[0];
        selecteditem.selected = true;
        var hasDocCoords = app.coordinateSystem == CoordinateSystem.ARTBOARDCOORDINATESYSTEM;
        var p = thisdoc.pageItems; 
        for (var i = 0, l = p.length; i < l; i++) { 
            var pID = p[i]; 
            if (pID.guides == true) { 
                var guideBox = pID 
        var wNum = guideBox.width; 
        var hNum = guideBox.height;
        var swNum = selecteditem.width;
        var shNum = selecteditem.height;
        var sxOffset = (swNum/2);
        var syOffset = (shNum);
        var xOffset = (wNum/2);
        var yOffset = (hNum-3);
        var xNum = guideBox.position[0]+xOffset; 
        var yNum = guideBox.position[1]-yOffset;
        var guideXCenter = xNum-sxOffset;
        var guideYCenter = yNum+(syOffset);
        var sxNum = selecteditem.position[0]+sxOffset;
        var syNum = selecteditem.position[1]-syOffset;
        //to test your script for position un annotate the two alerts below
              // alert("GuideBox Data:\nWidth: "+wNum+"\nHeight: "+hNum+"\nX Position: "+xNum+"\nY Position: "+yNum);
              // alert ("Selected object Data:\nWidth: "+swNum+"\nHeight: "+shNum+"\nX Position: "+sxNum+"\nY Position: "+syNum);
        //changes the position of the selected artwork to the center of the guide box.
        selecteditem.position = [guideXCenter, guideYCenter]   
    }//end centerart
function findguide()
var thisdoc = app.activeDocument; 
var p = thisdoc.pageItems;
var guidetoggle = false
        for (var i = 0, l = p.length; i < l; i++)
            var pID = p[i]; 
            if (pID.guides == true)
                var guideBox = pID
                var guidetoggle = true;
                }/*end if*/
            }//end for
        if (guidetoggle == true)
            //alert ("Found Guides")
            }/*end if*/ else
           // alert ("No Guides")
            artworkmax = true
            selecteditem.resize(99,99);
            }//end else
}//end function
function merge()
//function to merge both art and guide box
//when they are merged if the art overlaps with anything turned to guides
//it makes the guides disappear. So after you do this, run FundGuide if guidetoggle = False
//then the art and the guide overlapped
if (guidetoggle = true)
    var thisdoc = app.activeDocument;
    var p = thisdoc.pageItems;
            for (var i = 0, l = p.length; i < l; i++)
            var pID = p[i]; 
            if (pID.guides == true)
                var guideBox = pID               
                }/*end if*/
            }//end for
  var selecteditem = app.activeDocument.groupItems[0];
  //var artguidegroup = selecteditem && guidebox
  //var artguidegroup.selected = true;
  app.executeMenuCommand ('Live Pathfinder Merge');
  }//end if guides are present then run merge
  }//end merge function
function wait10() 
  while(a<100)  
    a++;
    if (a>99) break; // guard against infinite loop 
I had to up it from the 101% increase as it was bogging down the section if there were a lot of points but when I did it wasn't as accurate.  I'm going to set it up to enlarge by 5 percent - Collide then resize by "95.24%" then do it again at 101%
I had started on your path but my brain died when I got to around your number 7 so I started fishing for codes.
Thank you for all your help guys.