Conclusion for anybody searching and finding this thread:

The problem lies in pysqlite (python-sqlite) versions 2.5.2, 2.5.3 and
2.5.4.

The solution is to use 2.5.5 and later or 2.5.1 and earlier, at least
during the trac upgrade process. Failed upgrades can be resumed once a
working version of pysqlite is installed.

See the trac ticket for more details: http://trac.edgewall.org/ticket/9434

Caleb

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