$ 100,000+ US Dollars

If I had $100k to spend on lenses, I'd hire an engineer to design a programmable autofocus/aperture controller that speaks the Canon lens protocol, and build mod kits that interface with various current-generation manual-focus, manual-aperture lenses. Then, I'd sell them and use that money to buy camera gear on an ongoing basis.

And then eventually design and build a replacement for the Canon 50mm f/1.0.
 
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hmm, interesting

2x 1DX
1x 5DIII
1x 6D
1x of each L prime between 24 and 200 minus the 200/2.8
1x 200-400
1x of each 16-35, 24-70 and 70-200 f2.8 version
A half dozen 600ex-rt and two st-e3-rts

A nice trip somewhere with that lot and if there is still money left after that I would probably get a 600/4 and some other random assorted stuff like bags and memory cards.
 
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Heck, for that amount of money, one could get a full digital MF setup, IQ260 back, mini-ArcaSwiss Metric view camera for digital back, several digital grade MF view camera lenses for the ultimate in landscape photography - and still have some money left over for travel.
 
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