I'm posting this here for the 43oh and Energia community in case any of you encounter this issue.
I wrote a modified version of the SimpleWiFiWebServer example that compounded the HTML into longer strings, and discovered an odd bug in the way client socket writes are handled, at least when produced by a server listener (I've yet to confirm whether this bug exists on CC3200-originated outbound connections). Any attempt to run WiFiClient.write() with a length > 100 results in the SimpleLinkWiFi API reporting that everything is OK, but a traffic analysis reveals several bytes get missed or possibly duplicated from a previous write request.
To mitigate this problem, I've produced a modified WiFiClient.cpp which breaks up long writes into 100-byte chunks.
WiFiClient-writefix-E14.zip 4.66KB
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This WiFiClient.cpp goes into hardware\cc3200\libraries\WiFi
I have tested the original fault against a CC3100 w/ Tiva TM4C123 and was not able to produce the bug. So I believe this only afflicts the CC3200 for now.
An Energia github issue has been opened - https://github.com/energia/Energia/issues/545 - and I believe @energia is requesting comment from the TI CC3200 team on this bug.