The Mosh SSH client for intermittent connectivity ( https://mosh.org/ ) has definitely saved me at least 100 hours. Too bad that it's only available for Windows as a Chrome extension, and Chrome will discontinue support for it starting in the new year. Really not looking forward to having to search for an alternative...
Looks like it's available under msys2 on windows: https://packages.msys2.org/base/mosh
As an aside: msys2 mingw64 and friends are > 100 hours saved if you are a linux-soul in a windows environment. I don't think msys gets the attention it deserves.