As for the datasheets, what you refer to is the standardized Western templated datasheet. As I need more and more often, I am now used to the funky Chinese datasheets, and this doesn't hurt me eyes any more They are not as structured, as most of them are written and formatted directly by the developers, they don't have the luxury to have an in-house documentation department.
AFAICT, Espressif was built selling SDIO Wi-Fi chips for cheap Android tablets, and they have a huge experience in Wi-Fi RF, leading to their unique auto-calibrating RF design. But they took the MCU from Tensilica, and they probably just used it with only a few optimizations, having probably a staff of software engineers to work on the firmware. But this situation where you buy some prefabricated IPs is not uncommon, even at TI, NXP, etc. Leading to the same situation where part of the design are just unknown to the design team itself!
Don't mix Shanghaï-based Espressif who is making the chip itself, and all these Schenzhen-based companies who are just copying / optimizing the reference design to make the cheap modules.
Your experience with large manufacturer's support may be biased because you are probably working for a US-based company, and probably large enough to keep their focus.
My experience from a middle-sized European company is different: their support dropped to almost zero within a few years, and this is true for most of the major manufacturers. Generally, they prefer to acquire startups to integrate trending products in their portfolio, rather than invest on internal development and knowledge. They also favor recruiting sales representatives that will bring in money, than FAEs that will cost! Short time view...
Put shortly:
ESP8266 modules vs. CC3200 for commercial modules: NO
ESP8266EX chips vs. CC3200 for commercial modules: YES