I think of more and less safe as being correlated with more and less risk in the configuration.
The risk is typically assessed as the product of the likelihood of the event, times the impact of the event, should it happen.
High likelihood is usually associated with low impact, and vice-versa.
For example, failure of a neck o-ring on a tank is high-impact, but is quite rare, whereas failure of a second stage is much more common, but low impact...especially if it is mitigated by an alternative second stage.
What we normally do is try and mitigate with equipment and training and procedures all those "likely" things -- some of which have relatively higher impact, such as loss or non-availability of breathing gas; examples are alternate 2nd stages, dual first stages, and SPGs. We may also wish to try and mitigate some of the unlikely things (because they are usua;y high-impact), such as neck o-ring blowouts, dip-valve clogging, and manifold failures.
What we CAN'T validly do is simply count o-rings and say that fewer is safer. It is all trade-offs; if adding o-rings means adding risk-mitigation measures -- such as an alternate 2nd stage -- then it is OK to have those extra o-rings, because their unlikely failure is more than balanced by the usefulness of the alternate 2nd.
So, is an H-valve safer than a Y-valve? No....it only has one dip-tube and shares an air path for both second stages.
Is either safer on a single tank? Yes, because two first stages is better than just one.
Is a single tank with a H- or Y-valve safer than (a) manifolded doubles, or (b) independent doubles?
No, because there is only one air-supply with a single tank. That is such high-impact that the low likelihood of failure of the single-tank o-ring is no longer important; you need to mitigate this possibility, however remote. (b) is safer than (a), because the manifold is part of (a). However, manifold failures are rare, and isolation solve the problem in situ. That is why training with manifolded doubles emphasizes using the isolation valve.
@Angelo Farina says he has seen several failures of Y-valves and manifolds, both due to poor maintenance or handling. I would suggest the proper approach to mitigating those kinds of failures is better training, procedures, maintenance, handling, and NOT trying to have fewer o-rings.
We each have to decide where our own risk-tolerance is. Mine is with Sidemount for a high-jeopardy dive; total redundancy, no manifold, and I can see the valves and all the regs.