I've just started playing around with the CC3200 Launchpad as I'm also finding it tricky. I think it's definitely the CC3200 that's difficult as playing with the TM4C1294 Connected Launchpad and TI-RTOS beforehand wasn't too bad.
Here are some things I seemed to have to find out the hard way. Please correct me if you know better I've got anything wrong.
Flashing with CCS Uniflash
Connect using CC3x Serial (UART) Interface, not Stellaris In-Circuit Debug Interface.
The SOP jumper must be set to 2
You must power cycle the whole board if you change the jumper. Not just the reset button.
You can set the WLAN profiles in Uniflash. No need to use the "SmartConfig" which I had problems with. Select the profiles tab and check the "Update" box. Enter details for Profile1, etc.
/sys/mcuimg.bin is what's run when the board is powered up. Always this. Not the last debug session like on the MSP430 or TM4C.
Remove the SOP jumper if you've been flashing. Power cycle. Not just reset.
The dubugger is "Stellaris In-Circuit Debug Interface"
UART output is "CC3200LP Dual Port". Sometimes you can't start debugging if this is connected first. You can attach once debugging.
Your debug session is temporary. On reset it'll run mcuimg.bin code again.
Some examples use SSID defined with "#define SSID_NAME" (e.g. WLAN Station). Some use the config in flash (e.g. httpServer). Beware.
Watch that jumper to select station or AP (on P58). Stuff will hang if you set it wrong.
There's a new SimpleLink WiFi Starter Pro android app. A bit more usable, but it's still easy to screw up profile settings and get it to misbehave if you flashed anything other than the OOB code.
I think I've got my head round it now. Probably. The documentation is there but not easy to find and digest. The TM4C is much easier if you have an ethernet cable nearby though!
I have found examples that can be done with FreeRTOS or TI-RTOS. A bit of a pain to tweak things to compile, but if you follow the guides under SDK/docs/example you'll get there.
It is most likely to do with the network stack management. For simple superloop applications, bare metal code works, but when heavy network/usb stacks come into play, a small footprint real-time OS helps(in this case, TI-RTOS) to schedule and prioritize tasks. Hope this helps.