Its not needed to run the pc. But as you put it, its a really nice perk and once you have it you won't back to not having one. The deal is that because of the budget i included the ssd and not an hdd. So you don't have to re-install software etc. In you start instead with an hdd (around 50-60bucks) you will have the storage but the inconvenience i mentioned. So i proposed what i would do, buy the ssd now for 50-60bucks extra of what the hdd would be and get the hdd later.
The cpu comes with a stock cooler. It does what is supposed to but just that. I proposed a small/cheap aftermarket cooler which is decent for what you wanna do. Not do much noise and last you longer. If you wanted to go for high overclocks i wouldn't even link that cooler. The CM evo you linked is usually the cheapest decent cooler for small-mild overclocks.
Why go that route. You get so much more from a Z97 mobo. First off its not a 2-3year old B85 mobo, supports the latest tec and the next gen cpu's. Meaning will last you longer and its obviously better quality of a B85 mobo. Added bonus that if you change your mind with overclocking later...
W8 is said to be using a little less resources than w7. Do you care much about it? Probably not and its not the reason to buy it. But as with most things related into pcs, after some years things become absolete. Ie if you remember not very long ago XP support stopped. The same will come for W7. By having the latest software means you will have support for longer. If you had a w7 copy then not it would be worth to buy w8, but when you buy new i find it wise (think of it as an investment) to buy the latest. You can also make w8 look exactly like w7 and there is also the rumor that those with win8.1 will get a free upgrade to win10.