I think the new TI CC3100/CC3200 support SSL on board, but I don't know if the distributors have silicon availability yet.
Yes, CC3100/CC3200 look good. Mouser says it will be available in Q1/2015. How difficult is it for a non RF guy do use it in design? (FCC and maximizing range are not required).
They will also have modules which I assume will be pre-compliance tested.
I've been using the CC3200 and CC3100 for a few months now, but only on the boosterpacks, there is no standalone silicon available yet. The CC3200 includes an integrated ARM core, whereas the CC3100 is designed to hook up to an extenal microcontroller through SPI. Most of my work has been on the CC3100 with a non-TI microcontroller. Porting the API from TI was reasonably simple and is positively encouraged. In contrast, Microchip's WiFi modules are only supposed to be used with Microchip parts.
I have managed sustained 14Mbps UDP throughput with both the CC3100 and CC3200. The Microchip WIFI 802.11g modules are lucky to make 5Mbps, and even at that rate your processor has to be paying full attention to the SPI bus that the device is connected to with almost nothing left over for anything else.
The methods TI have to allow connection to the CC3x00 are quite clever although I am not sure how robust some of the methods would work for non-technical end users.
But as has been said, there is no production silicon yet for the CC3x00 and the distributor release date keeps receding, while TI are saying nothing. It is quite possible they're stuck in compliance testing woes. I am contemplating releasing a product with a set of pin headers that just so happen to mate with the $20 dev module. Not a use case for my own compliance testing of course ;-)
Edit to add: Regarding using in your own design, either use the forthcoming (expensive) module, or start with the dev board aka booster pack as a starting point, and make sure your board layers are the same. From my own experience, the best way to learn about what works and what doesn't is by doing. Having equipment and methodologies to confirm your designs quantitatively is essential for producition stuff, not so much for hobby stuff. There is also a world of difference between fiddling around with short wave stuff and 2.4GHz.