Thanks for sharing your story; as a developer/designer (more developer than designer; love C, no love for JavaScript), I hear stories such as yours practically everyday.
What I really wanted to say is that I love your aviator gopher and the designer should have at least taken a shot at incorporating your gopher in the logo.
I mocked-up a negative space [almost] one-colour logo with a close-up of a stylized gopher nose and teeth wearing aviators on a CRT green background with a brighter green cursor reflecting in the glasses. That ties in your history for continuity, modern pilot with aviator glasses, a cursor for remote control, and the green background as a nod to the past.
Growing up on green and amber CRTs, I'm a huge sucker for retro designs, and try to incorporate Rand Paul's philosophy wherever I can, which captures the essence of a company in a clean and easily recognizable design.
I'll take the blame for dropping the chipmunk. I wanted the logo to appeal more to businesses, and I felt like the chipmunk came across as too playful, so I told them not to bother preserving it.
Ah - thanks for having a look and responding with a nice comment. I suspected what you wrote after I posted, since I have many people asking for the the next iconic "f" or "G" or Apple, and I usually tell them that the logo should instantly recognizable as your own (for whatever that's worth). Paul Rand's (I think I wrote Rand Paul above!) "Thoughts on Design" is a great short book where he says, "...[a design] is not good design if it does not co-operate as an instrument in the service of communication."
Above all, it's important that you love your new design (you mentioned that you do), which is great and positions you for growth in your target areas as opposed to "preaching to the converted," which is what I think you're implying with the chipmunk.
I love the airplane/shell prompt thing in the new logo, though. Having never seen TinyPilot before this, I had no attachment to the chipmunk, and I agree that the change moved from hobbyist to business vibes.
What I really wanted to say is that I love your aviator gopher and the designer should have at least taken a shot at incorporating your gopher in the logo.
I mocked-up a negative space [almost] one-colour logo with a close-up of a stylized gopher nose and teeth wearing aviators on a CRT green background with a brighter green cursor reflecting in the glasses. That ties in your history for continuity, modern pilot with aviator glasses, a cursor for remote control, and the green background as a nod to the past.
Growing up on green and amber CRTs, I'm a huge sucker for retro designs, and try to incorporate Rand Paul's philosophy wherever I can, which captures the essence of a company in a clean and easily recognizable design.
Edit: here's just the gopher for the curious: https://imgur.com/a/OEk8IUL