The anchor seems a bit random. Why is GrayStudio instagram seems to be promoting the old light bulb logo for V2 when the board seems to be heading toward the anchor logo. A unified branding will creates a stronger branding. It creates confusion when the front is a light bulb yet the back is an anchor. Be consistent with branding when doing promotion, a style guide will help with that.
Love both. From outside perspective, the light bulb seems to emote "Think6.5 v2.0" while the anchor says "ReThink6.5". If you are mixing both of the logo on the same board, then one of the logo will look like an "after thought".
However, I understand doing a redesign is hard: you want to retain the old audience while pushing changes. From my experience, if you want to create a new look and feel, you have to be bold. Being consistent will make the design more holistic. Right now, the front of the board doesn't seems to speak the same design language as the back.
This summarizes my feelings on the whole anchor theme. The thing that makes Think unique as an enthusiast board is that it already has a following because of a strongly established look and brand; to change it while keeping it named the same betrays expectations, and potentially leads to disappointment.
Right now I think the design is suffering a bit of schizophrenia because it incorporates elements that fans recognize (the name, the lightbulb) but combines it with thematic elements that don't make sense (the sailboat, the anchor). If you had to rely on a paragraph of text explaining the meaning of those new elements, is it successful as a design?
Granted, I understand how oldcat feels - the anchor theme is something that he and his wife love on a personal level, and it's clear that he has an investment in making improvements and doing something different than before. But I would counter that oldcat should probably THiNK about just making it a new board with a bold new design instead, so that people have the right expectations about it. Personally, this would have been an insta-buy for me if it were just a design refresh of the Think6.5 with a gasket mount and a more seamless design - but the misplaced nautical elements are enough for me to reconsider.
This is the exact problem of inconsistent design language and branding. When your audience wants you to engrave "THiNK" into the board, a light bulb should pop up and make you think why engraving "THiNK" was necessary. I'm not saying this is good or bad, just something to think about.
Now, this is completely my opinion. I think the brand Think6.5 is too deeply connected with the light bulb. People associate Think6.5 with the gear looking light bulb. So when you presented them with an anchor, even after paragraphs of story and description, they still want the "Think" to be engraved on there. A logo identifies, not describe -- I'm quoting Sagi Haviv and Brian Collins (Haviv did branding for National Geographic etc. and Brian Collins did Spotify etc.). Adding "v2.0" seems like a cheap compromise just for brand loyalty retention.
Again, this is purely on the branding perspective. Nothing I said was about badge placement or case design. However, to me, branding helps guide the design. Without a clear branding, it is hard to achieve a holistic design.