intel processors are known for their great single core performance. amd processors are known for their integrated graphics(apus) and more cores(fx series). with the i7, although there are less cores, they are more efficient cores than the amd cores. the performance differences arent alot, but other factors sway the decision more in my opinion. the 9590 i think is a 220w processor, where the i7 is only 130w. this also is the heat factor, the 9590 will run alot hotter than the i7. this will lessen the length of the processors life (minimally in my opinion) and will be hard to cool. but your going with water cooling, so you should be fine.
for the cpu upgrades, amd isnt looking to upgrade their architecture for the fx series processors through 2014 i think, maybe not even 2015. so upgrading from the 9590 is doubtful right now.
for broadwell, if theres a socket 2011 cpu then you can upgrade, will it be worth it? maybe, you never know until broadwell comes out
motherboards: im sure the msi board will do fine, i'll look more in depth but it will take me a few more minutes. the asrock killer looks good, i was thinking of getting it for my 8350 build to overclock. i'll check the asrock website to see if it supports the 9590
also, you can't overclock the 9590. it is already overclocked nearly to the max, and without an extreme custom water loop the temps will skyrocket. with the i7, you can overclock it, and alot. id say atleast a 1ghz bump up with good cooling.
in conclusion, the stock i7 and the 9590 are about the same in performance. the i7 makes up for less cores and clock speed with performance, while the 9590 makes up in less single core performance by higher clock speeds and more cores. i would overclock the i7, which can make it to 5ghz. that overclocked i7 will beat the 9590.
one final thought which only you can decide on: future proofing. theres no way to actually know how long components will perform where they are today. games may use more cores, however the most they use today are 2 i think. games may utilize more cores in 1 year, or it may be 10 years. theres no way to really know. i think today, you will get better performance out of an overclocked i7 than the 9590. in the future, i think the overclocked i7 will be matching the 9590 if games utilize cores. but this probably wont be anytime soon. so i do believe its worth the extra money.