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I replace the batteries in my UPS every 18 months, and don't try to outlast power outages.
I have everything configured to shut down if the power goes down and stays down more than 5 minutes, which is ~20% of the maximum rated runtime. (I'm using repurposed desktop hardware that loves it's watts as a home server.)
I picked the low number for the reasons you've outlined: even if the battery is severely degraded, it's probably not THAT severely degraded and it's a safe time span to ride out short hiccups, but still well under the runtime limits so that a safe shutdown can happen.
That and I've noticed that, typically, if the power is down for 5 minutes it's going to be down for way longer than 5 minutes, so it doesn't matter and I'm not going to have enough batteries to outlast the outage.
Plus lead acid batteries hate being discharged at all. But deep charge cycles are really awful for them.
That said changing batteries every 18 months is a little excessive. Unless your UPS is overcharging the shit out of them they should last way longer than that.
Little bit of A, little bit of B.
I probably go through at least one full discharge cycle a month, if not more because the power around here suuucks. (The NAS goes down, but I leave the network gear up until the UPS dies, because fuck it, why not.)
It's also a ~10 year old UPS that likes to eat a $25 battery every 18 or so months so I just haven't really had any justification to replace the whole thing yet since there's an awful lot of $25 batteries in a new UPS.