It seems that the choice is whether to live on the slightly-bleeding edge (as determined by “stable” releases, etc), or to live on the edge of end-of-life, always scrambling to rewrite things when the latest dependency library is being officially obsoleted. I advocate doing the former, while you seem to prefer the latter.
The problems with the former approach are obvious (and widely seen), but there are two problems with the latter approach, too: Firstly, you are always using very old software which are not using the latest techniques, or even reasonable techniques. This can even be considered to be bugs – like using MD5 hash for example, which, while being better than what preceded it, much software were using MD5 as a be-all-and-end-all hashing algorithm; this turned out later to be a mistake. The other problem is more subtle (and was more common in older times): It’s too easy to be seduced into freezing your own dependencies, even though they are officially unsupported and end-of-lifed. The rationalizations are numerous: “It’s stable, well-tested software”, “We can backport fixes ourselves, since there won’t be many bugs.” But of course, in doing this, you condemn your own software to a slow death.
One might think that doing the latter approach is the hard-nosed, pragmatic and responsible approach, but I think this is confusing something painful with something useful. I think that doing the former approach is more work and more pain from integration, and the latter approach is almost no work, since saying “no” to upgrades is easy. It feels like it’s good since working with an old system is painful, but I think one is fooling oneself into doing the easy thing while thinking it is the hard thing.
The other reason one might prefer the former approach to the latter is that by doing the former approach, software development in general will speed up by all the fast feedback cycles. It’s not a direct benefit; it’s more of an environmental thing which benefits the ecosystem. Doing the latter approach instead slows down all feedback cycles in all the affected software packages.
Of course, having good test coverage will also help enormously with doing the former approach.