In the Portfile you've written
depends_run \
port:py-bob.blitz \
port:py-bob.core \
port:py-bob.io.base
outside of any blocks or conditionals. That means it applies to all ports, both the "main" port and all the subports. So, for example, you've asked the subport py-bob.blitz to have a dependency on itself, which of course can't work. If you only want the main port to have those dependencies, say that:
if {${subport} eq ${name}} {
depends_run \
port:py-bob.blitz \
port:py-bob.core \
port:py-bob.io.base
}
But there are additional problems here. You're using the python portgroup, whose purpose is to let you create one port (named py-something) and it will create subports for you (named py26-something, py27-something, py33-something, py34-something, etc.) based on how you set python.versions. But then you're trying to create additional py-somethingelse subports as well. The python portgroup doesn't know anything about these other subports you've created, and will not create py26-somethingelse etc. subports for you, so that won't work right. Furthermore, these subports are all for different software, which have their own version numbers, master_sites, distfiles and checksums. I think you'll find things will work correctly if you create a separate portfile for each software, and not try to put them all into the same portfile.
If you need further help developing portfiles, please write to the macports-dev mailing list rather than filing tickets in the issue tracker.
