Ah yes... the Mille Miglia's...
They are nice, I want to get one as well...
While the Madison would be the wise choice financially (resale value), aesthetically I think the speed black looks better. IMHO watches should be bought to wear, use and look at - not solely as an investment... so go for the Speed Black if you think you can get it (Chopard store on Rodeo?).

I have a bunch of nice watches, yet only one that is solely an investment and remains unworn/new in its box.... and still it hurts and sometimes I have an urge to unpack it (but I won't). Buy nice watches that you wear and never sell one unless you have to!