SSD - yes, I've had a Samsung 830 Series 120Gb SSD for nearly three years now. It's faster than my system can handle (SATA speed). I've also had it partitioned into 80Gb and 40Gb partitions for dual-booting my "Work" and "Gaming" Windows, respectively. Both partitions have less than 10Gb free though, which is why I jumped on the chance to get another, larger SSD as I mentioned a few posts up.

i7's main advantage lies in it's hyperthreading which is very usefull if you use programs that can use 8 cores.
In those cases an AMD processor can net you similar performance gains for the smae price as an i5, but your single thread performance suffers.
Or you can indeed spend it on an i7 but that could mean that you spend a lot of extra money for a feature that you hardly use. I know of only two games that actually use 8cores or hyperthreading: Rome 2 total war and Battlefield 4, even though 8 cores have been around since 2011...
Anyway
Just get the i5
I'm more likely going to get more use out of multiple cores/threads due to multitasking rather than through a highly multithreaded app, so when push comes to shove, 4 cores/4 threads is probably going to be just as effective as 4 cores/8 threads. The only reason I could see to go for an i7 would be the higher clock speed, but practically, I don't think it makes enough of a difference.
Sandwich, it's a solid plan and all those i5's should serve you well. 16GB RAM is also good choice and as many others have recommended, so would be an SSD.
I would strongly recommend getting a GPU that has 4GB GDDR5, Radeon R9 270X or GeForce GTX 760 would be good choices for budget conscious who still want decent gaming performance. If you have a bit more money to spend, then you really should aim for a GeForce GTX 970 though.
You should also carefully examine what ports are available on each GPU, most GPU's have one DVI-I, one DVI-D, one DisplayPort and one HDMI. If that's sufficient for your needs, then you have plenty to choose from. Otherwise your options become a lot more limited. I recently bought a GTX 970 and went with Gigabyte since Gigabyte has the only model with three DisplayPorts.
Until about a year ago, I was still running a GeForce 8800 GTX.

It finally gave up the ghost though (in all fairness, I
did let butter drip all over it like 6 years ago...), so I replaced it with a GeForce GTX 660 Ti. It's "only" got 2Gb GDDR5, but like my SSD, I'm pretty sure my Core 2 Duo and/or motherboard have been preventing it from performing at full speed. Anyway, I'm not planning to upgrade that anytime soon, especially since for whatever reason, 3D monitors haven't really taken off here at all - they're simply not available. Ah well.
One thing that occurred to me today though is power... my PSU is a Thermaltake Litepower 600W, and I honestly have no idea if that will be sufficient for my upcoming upgrade. From what I can tell, the TDP of my E6600 is 65W, and the potential Core i5 processors are around 84-88W. I suspect that by itself will be fine, but what about the other system components - motherboard and RAM? Do those somehow consume massive amounts of power?