I have some legacy linux servers that need an update to a new OS. Is Debian 8 a good choice? All I care about is that stuff just works for as many years as possible, gets security updates and does not break.
Debian 8 has support until 2017. Ubuntu 1404 LTS has support until 2019. RHEL 7 has support until 2024 (and Centos).
So in practice you don't get a larger number of supported packages than with RHEL/CentOS.