It seemed like it'd be well supported, and also well optimised for ARM (which basically every uC apart from ESP8266 is using). It also exposes SHA/AES/MD5/etc that would be useful to Pico owners in their own right.
I think the only thing stopping a lot of people using PolarSSL was the licence, but since it got acquired by ARM they moved to something far more permissive.
For ESP8266, it could be worth setting MBEDTLS_SSL_MAX_CONTENT_LEN in config.h and actually seeing if it can connect to any services. My guess is that stuff like Twitter won't support it though.
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