In your examples, you're comparing locking down a system and letting it age.. vs upgrading and fixing things that are broken.
The difference here is the amount of labor. In your first example, you propose no labor investment.. and in the 2nd, regular investment of labor. Of course that results in the 2nd system being better. If you invested the same labor required by your 2nd example in the 1st, you would likely have an equally usable and up to date system. Similarly, if you didn't invest any labor in the 2nd, you would have a broken unusable system (since the bugs would never get fixed).
Another way to think about this is that as systems age (bugs are found, exploits, etc), they create technical debt. You need to invest the time to address that debt, or you will suffer later down the road.. same as most tech debt.
The difference here is the amount of labor. In your first example, you propose no labor investment.. and in the 2nd, regular investment of labor. Of course that results in the 2nd system being better. If you invested the same labor required by your 2nd example in the 1st, you would likely have an equally usable and up to date system. Similarly, if you didn't invest any labor in the 2nd, you would have a broken unusable system (since the bugs would never get fixed).
Another way to think about this is that as systems age (bugs are found, exploits, etc), they create technical debt. You need to invest the time to address that debt, or you will suffer later down the road.. same as most tech debt.