To answer #1, here's a not-so-great way to find a random point in a path: http://jsfiddle.net/Aj7Rw/
var points = [[73, 192], 
              [73, 160], 
              [340, 23], 
              [500, 109], 
              [499, 139], 
              [342, 93]],
    minX,maxX,minY,maxY;
// find min and max values
for (var i = 0; i < points.length; i++){
    var point = points[i];
    if (minX == undefined || point[0] < minX)
        minX = point[0];
    if (maxX == undefined || point[0] > maxX)
        maxX = point[0];
    if (minY == undefined || point[1] < minY)
        minY = point[1];
    if (maxY == undefined || point[1] > maxY)
        maxY = point[1];        
}
// draw the path so we can use isPointInPath
var can = document.getElementById("test"),
    ctx = can.getContext('2d');
ctx.beginPath();
ctx.moveTo(points[0][0],points[0][1]);
for (var i = 1; i < points.length; i++)
    ctx.lineTo(points[i][0],points[i][1]);
ctx.closePath();
ctx.stroke();
// generate some random points. 
for (var i = 0; i < 250; i++){
    var found = false, iterations = 0;
    while(!found){
        iterations++;
        var x = Math.floor(Math.random()*(maxX-minX)+minX);
        var y = Math.floor(Math.random()*(maxY-minY)+minY);
        if (ctx.isPointInPath(x,y)){
            found = true;
            ctx.fillRect(x-3,y-3,6,6);
            console.log(x,y, iterations); // I'm logging the number of iterations it took to generate a point within the poly so you can get an idea of the lack of efficiency.
        }
    }
}