I have to disagree with you. The site went from a basement project look-and-feel to something much more slick and credible. I'm with you right up until the point where people are paying for TinyPilot out of the business account; then the brand credibility really matters.
Touche! Probably why slack went from edgy logo to looking like an Atlassian product line. Didn’t get fired for choosing X. I might be wrong then in that light. But I would personally have been more drawn in by the OG design.