Stale cache handling with a persistent object cache

Lets say you are doing an update_option() and because of some temporary network glitches updating the value in Redis/Memcached fails and you end up with a stale cache for a specific option key. The core APIs does not seem to care about the response from wp_cache_set() and they move forward with the rest of the process. Then the subsequent updates could delete or revert that option value in DB and that could have major consequences for the app depending on what that option value is used for. How do you handle this? How is this handled in large-scale WP setups? Anything that can be improved in core?

How do you avoid caching during development?

Is there a simple way to prevent all caching when testing the appearance of changes to the site? I use WP Super Cache. I can delete its cache using the option provided, delete the cache for my browser, and still some changes to CSS or widgets do not refresh. I try other work-arounds like switching browsers or computers, but there must be a more stream-lined workflow where I can ensure I’m viewing the changes I made and not some cached earlier format? What’s the best solution for this?