Not sure what your real question is above.
Keeping two separate families might be an unrealistic example but if you have wife and kids both in Tokyo and Dallas, you can say both:
東京とダラスで並行
して生活を送る and
ふたつの街で並行
した生活を送る
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My best guess is that 並行して would be used when you're talking about two things happening at the same time, but 並行した would be used when you're specifically talking about one of the things that is happening.
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Not really. As you can see above, both して and したcan be used to refer to both of the two items in question.