Of course strings are drawn upside down; the text rendering code written by Microsoft was written with the understanding that the Y axis is "flipped" as you put it. If you apply a transform to turn it the other way up just so your brain can work it out, the existing code doesnt take note of the transform.. It carries on drawing as if 0 is the top, and everything is rendered upside down, even dropshadows on boxes etc.
Another way to look at it is; if a programmer at microsoft is smart enough to learn how to think in "0,0 is top left" then you are too. Reprogram the way your brain thinks about this, dont try and transform it to the coordinate system you were taught in primary school..
The reason we teach infants to go up and right is because, standing on the ground, they cant go downwards only upwards. They also dont understand negative numbers and are told that it's not possible to have 2 apples and take away 3. They usually write from left to right which explains the positivity of both the axes.
School is a gradual refinement and correction of lies told because the brain at a certain age isnt really capable of logically appropriating the actual truth. Here's another refinement: Computers draw top down, left right. Know this, and get on with it