yup, this is a real problem with small community sites that drupal is other wiser awesome for. the work involved can be rather arduous (and impossible if you are using a module that lacks an upgrade path).
that said, the drupal community is huge and in my 8+ years of building and running sites i have always been able to work out an upgrade solution, finding the time to implement it is the bigger problem.
Last I used it, there was still too much that the Features module didn't 'cover', making it less useful and sometimes even counter-productive for me. Has this improved greatly in the past year?
Configuration management can be a real issue. For Drupal 8 there is the Configuration Management Initiative meant to solve just this problem. It will be there in Drupal 8.
Features has some very rough edges. It's a bolt on after the fact solution. Through it Drupal developers learned about the rough edges, what people want here, and so forth. What comes in Drupal 8 is meant to be a proper solution at the core from experience.
that is generally what the features module is used for http://drupal.org/project/features
> which makes upgrading incredibly painful
yup, this is a real problem with small community sites that drupal is other wiser awesome for. the work involved can be rather arduous (and impossible if you are using a module that lacks an upgrade path).
that said, the drupal community is huge and in my 8+ years of building and running sites i have always been able to work out an upgrade solution, finding the time to implement it is the bigger problem.