Hi Esteban,
I'm not sure my answer will please you or stef, and maybe I shouldn't voice it, staying being a "customer" instead of contributing "the way you want it". Hard words, but yours are hard too.
I'd say simply that Pharo is successfull, fairly successfull for someone like me. It allows me to engage in complex work, in what I do best and what affords me to be paid and have the freedom to use Pharo. Some of those things suppose that I maintain and extend fairly complex packages on top of Pharo, and deal with permanent, multiple overlapping interruptions (meeting, administrative work, travels, etc...). Pharo is great, it allows me to build a significant activity on top of it.
Some of the consequences of that success? I'm looking at things that works now, not in Pharo 5, 6, or 7. I'm a bit frightened by grandiose rewritting attempts which will be usable in a version or 2, at best, and leave an unsatisfying "now" situation. I'll carefully evaluate what new stuff is integrated. New stuff I look to see if they are usable (libcgit integration, TxText) and what I see is stuff that builds on unstable core libs extensions (NativeBoost, Athens) on top of an already unstable version (4.0), and I'm really not impressed by the software development process.
The end result is, when I see a bug, I'm already at least two versions behind you guys... so there's nothing worth reporting. There is some progress on the way things are being done (thanks Marcus for doing the deprecation API backporting on 3.0) and not much on others (and I speak of methodology, not of new features being added on).