The problem is that the size of the para object is determined dynamically when it is drawn. At the time you create the second para, nothing has actually been laid out yet, so a width hasn't been set. You can see that accessing the width after drawing works as expected:
Shoes.app do
p = para "My width is: "
@para = para p.width
button 'Get Width' do
@para.text = p.width
end
end
The way to get around this is to use the start method, which is called when the containing slot is drawn for the first time:
Shoes.app do
p = para "My width is: "
width = para p.width
start do
width.text = p.width
end
end