Five gems? I haven't seen very many production Rails applications that can do with just five gems. More gems is mostly a good thing - each does just one thing, and does it well. It is like having more smaller methods instead of a few large methods.
> Are these gem heartburns a common problem in Ruby/Rails or is this mostly due to my ineptitude with the language?
Yes, gem heartburns can happen, but they are not very frequent. I'm sure the author will find that Bundler makes versioning an almost solved problem as he understands the language and ecosystem better. Good luck!