dragonchild,

I've written an almost exact reproduction of Minesweeper (look-n-feel wise) in Perl using the Tk GUI toolkit. The code is simple and well-documented, and the program works perfectly on Win32. You can download it from here. It will show you how to use Tk's Canvas to achieve what you want.

Package / install - wise, it's even simpler. The excellent PAR module has a "pp" program in it that creates executables (complete, self contained Win32 .exes) from your scripts, including all the dependencies (like Tk). A GUI application with Tk will weigh around 2.5MB, will take a few seconds to load the first time it's run (it unpackages stuff to the Temp directory) and then run almost instantly.