Kicking the can down the road
I tend to think keeping stuff running on an old but supported OS is in the long term not such a good idea,
It is going to have to happen at some time so why not do it when you still may have institutional knowledge.
After 5 years it is quite possible you may not have the people who know why it was built the way it was.
Perhaps a newer OS may have solutions to the issues you had to work around but what if no one remembers what they were?
Finally often the OS is only what the software stack sits on and whilst you can patch the OS what about what is is running on it?
Well only my 2d.