If I go with debian, which has a much different release cycle as ubuntu in general, what are the ramifications of this choice?
It means you don't have to upgrade your machine every six months.
From what I understand, I will not be able to use the package management to automatically install software/patches correct?
No, that is completely incorrect. Debian provides security updates and critical bugfixes as long as the OS is supported (which is significantly longer than most Ubuntu releases).
So that means I will have to download and install whatever I need manually then? (install or actually compile?)
Not in general, but it's an important skill to know regardless of what distribution you run, because sometimes you need to run something that isn't packaged for your distribution. I consider it a core sysadmin skill.