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docs say that CiviCRM does not support shared SSL and "SSL must be installed on your domain not one at a higher level"

What about subdomains?

I have WP installed at site.com and WP with CiviCRM installed at civi.site.com

Do I need to be able to install SSL on civi.site.com or will it work from site.com?

2

There is nothing specific about civi on your question, it is possible to use a wildchar certificate (*.site.com) or one that works for several subdomains.

If you want a simple and free certificate and that isn't offered by your hosting company, I recommend you "let's encrypt".

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