I find the presentation confusing, to be honest.
Now, please excuse the shouting, but your question and your website both capitalize the product names, so I'll follow suit.
You have 'BASIC' - $9.95 per month. Let's consider that the baseline offer.
'PREMIUM' offers three additional features, and extends one feature (data retention 6 months not 3), priced at $19.95. Let's take as read that this is good value - you'll already know from your analytics. So this is very much the standard 'level up' product.
But then, there's 'PRO.' PRO is feature identical with PREMIUM, but extends one feature (data retention 12 months not 6), and is charged annually in advance. So the question is, what is PRO? Well, you need to decide.
It could be another product level - and as it's another column in your table, it has its own tick boxes, and it has its own name, I think that's the expectation. But it's presented as being priced below PREMIUM, which is confusing.
From your question, what you seem to mean PRO to be is not a distinct product level, but simply a payment option: you want to reward a 12 month up-front payment with a discount.
If that is what you want, then say it. Offer it as an option within PREMIUM, and present it not as a freestanding dollar amount but as a discount or bonus - $25 off, or 10% reduction, or 12 months for the price of 11, or...
And then you need to decide whether you should make a similar offer on BASIC. I'd argue that if the term discount you run with is moderate, you should offer it on either BASIC or PREMIUM.
You need to make the presentation coherent before you can optimize the price.
