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You can use the divisibleby filter:
{% for skill in person.skills.all %}
{% if forloop.counter|divisibleby:"5" %}
<div style="page-break-after:always"></div>
{% endif %}
{% endfor %}
That will add a page break at every row that is divisible by 5 (ie. 5, 10, 15, etc).
Source:stackexchange.com