Theme under the premium plan
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I am considering signing up for the premium plan. However, I have a few concerns. I currently have a free plan and the admin section is nothing like a hosted WP site. I assume this is because of the limitation of a free site. However looking at the bullet points of the premium plan it says hundreds of free themes, but there are thousands out there so does that mean one is limited to a few hundred hand-picked themes? I just don’t want to sign up and then not have the options I would with a host wordpress.org site.
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WordPress.com is never going to offer exactly the same freedom that a self-hosted WordPress.org site does. That’s part of what you trade for the stability, security and ease of hosting that you get with WordPress.com.
To answer your question, no, you will not be able to upload themes downloaded elsewhere to your WordPress.com site even if it has the Premium upgrade. You can see a list of available WordPress.com themes here:
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