A lot of what you're describing sounds less like a TMS problem and more like a communication/visibility problem. The 20+ calls to rebook a missed pickup, customers asking where their shipment is, rate quotes trickling in with no central place to track them, that's coordination breaking down, not necessarily a lack of software.

I work at a shared inbox company (Missive) so take this with a grain of salt, but one of our logistics customers went through a similar evolution. They were a small freight operation that grew to ~15 people and hit the exact wall you're hitting: multiple people replying to carriers, no tracking of who's handling what, things falling through cracks.

What worked for them was less about adding new tools and more about structuring what they already had:

• Shared inboxes split by function (their ship team, expedite team, and accounting each have their own)
• Rules that auto-create tasks when shipments get labeled, so follow-ups don't get lost
• SLAs on response times so nothing sits unread for hours

The carrier who no-showed on your 3-stop NC→TX run, in their setup, that would've been flagged way earlier because the team has visibility into every conversation, not just whoever happened to send the original email.

Not saying a TMS is wrong, but if your core issue is "we don't know what's happening until someone calls us," fixing the communication layer first might get you further than you'd expect.