Sure, but that's your experience as an individual developer on a small component of the system. If we're looking at the health of the system _as a whole_ (of which you, and the work you're doing to solve these issues, are a part), it's completely resilient to this change.
Funny you should say that w.r.t. to reliability.
I just got back from vacation today and have just had 2 SSL-related issues I needed to solve, not to mention one related with dependencies on smaller components, which when updated broke my chain of software.
All these would have worked more reliably 1. without HTTPS and 2. if everything were packaged together :)
In short, the simpler solution would clearly be more reliable here.