You do not need an SSD; I work with huge images and video games and while an SSD helps with speed performance, its really only 5-10FPS at most and you may end up burning it too fast with update writes. I'd suggest the smallest 1080p monitor you can find (personally I prefer high DPI over stretched images). I'd suggest a 600w power supply, and the first case you suggested should fit almost any graphics card you throw at it (just don't do that literally). You can also use programs like CRU to add 1920x1080 to monitor that don't "support" 1080p; some monitors are sold with forced down EDIDs even when the pixel count it much higher than the max "native" that the EDID provides. For a main drive I would suggest getting a fast, large mechanical drive rather than a couple smaller ones because while an SSD is fun and fast, it gets to be a pain to setup locational based events (downloads, installs, documents and media; similar to small main drives; ie 160- and 80GB mechanicals). I own a WD Black 2TB SATA 6GB/s drive and it serves me well as a main OS dual-booted drive.
(update) If you can find a GTX 750(for a cheaper price) it might suit you better if you don't intend to do anything demanding and you could fit it easier under a 500w roof. I'd suggest buying an aftermarket fan no matter what, Intel fans are pretty much garbage for extended use.
-H87 chipset motherboard since you're not overclocking.
-Better quality psu.
-Better quality case.
1. SSD is up to you.
2. No, the stock cooler should suffice.
3. Yes, but the cougar psu isn't very good quality. This XFX one is high quality.
4. Yes, but the Corsair 200R is a better quality case.
5. 23" is not necessary, as 1080p monitors can be find in a variety of the sizes. 23" is just the standard norm because 21.5" is a bit small for people. If you're fine with 21.5" or 22", then go for it.