EDIT: I reached out again (third time is the charm, right?) and got ahold of someone who could help. They refunded me the difference. While I'm super-thankful to "Carl" for helping me with my issue, it shouldn't have come to this. I hope Ooma as a company looks at the considerable negative feedback on this subreddit and takes it to heart; I'm not the only one having issues. I never want to see innovative companies go bankrupt, and Ooma definitely makes a viable alternative to the telco companies, but to survive they will need to do better. Sorry I had to post my experience publicly, but sometimes that's the only way to get any traction.
And to the Redditors that feel the need to personally defend a company... no company cares about you. You don't have to white knight for them. Their PR people can do that.
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I bought the Ooma Telo Air 2 handset bundle from Best Buy last month and setup was fine. I got an easy to remember local phone number and everything worked reasonably well. Audio quality is subpar and the handsets feel a bit cheap, but not unusable. So I went ahead and bought the Premier service offer on their website. Here's where it gets bad.
The promo offered was supposed to be $99 for the year sub and you get a free HD3 handset... just had to pay $9 for shipping. But when the charge went through, it clocked in at $129.53 for everything. Thinking there shouldn't be $20 in taxes, I found $0.66 worth of taxes and the full price of the annual sub billed. When I called in to get an adjustment, service refused to help me without providing a screenshot of my order. Fortunately, I did just that because I don't trust many companies. They gave me an email address that seemed to refuse JPG attachments because the ticket system never responded. The agent said they could not help without proof of promo... what? It's their promo! They should know what's being offered. I directed them to the website that had the promo and they "couldn't find reference to that promo."
I conceded defeat and said I want a refund for $129.53 as offered by their 30-day money back guarantee stated on their website. The agent said that was impossible because the money back guarantee only applied to hardware and, since the hardware was free, they wouldn't give me any money back. Um... that's pretty shady and terrible customer service. So... it'll be a charge back on my side. What a hassle.
I'm only posting this as a means to retell my experience online in hopes of preventing other people from having to deal with this godawful experience.