Just adding my support to measured movement as well.
From a usability standpoint, to toggle between movement and measurement using a toolbar button is a recurring cause for confusion. A keyboard shortcut for measurement is a must (currently Command+F brings up a drawing tool, I thought "Path" would refer to measurement!)
In truth, people need to switch back and forth between measurement and movement in a much cleaner, faster way that is currently allowed.
My suggestion:
Click and Drag a Token leaves a measured Path.
--- Space bar (or right click) drops waypoints.
--- Escape key clears the path and returns token to the original position
Shift Click and Drag anywhere on the map is a measurement tool.
--- Space bar (or right click) drops waypoints.
Shift Click and Drag from a token behaves as a measurement tool, but highlights the token.
--- Releasing shift before releasing the mouse button moves the token to the mouse cursor position and treats it as though you have dragged the token to that point.
--- Space bar (or right click) drops waypoints.
--- Escape key clears the path and returns token to the original position (if shift released)
Yes. That is brilliant. There are only a couple hurdles left to clear before my group abandons MapTool and commits to roll20, and this is one of them. Essentially, "When measuring distance, the first diagonal counts as 1 square, the second counts as 2 squares, the third counts as 1, the fourth as 2, and so on." [d20 rules] It'd make combat that much easier, as manual calculation of movement is something we erased by adopting MapTool.
If I remember correctly, the problem with tracking automatically the movement points whilst moving, is that the system breaks down as soon as there are different costs for different types of squares and even for different types of obstacles between squares.
I don't think the OP wanted anything so granular. Difficult terrain or different movement types is something the GM has to handle manually. All we're really asking for is the square of the hypotenuse of a right triangle to NOT equal the square of its next longest side.
Essentially, if two characters have to hit a switch across a room with an ogre in the middle, one character runs straight for the switch right past the ogre and another takes a wide swath avoiding the ogre, the guy risking getting crushed to goo should arrive at the switch before the character who respects the better part of valor.