RoadRunner Auto Transport
RoadRunner makes this list for the same reasons it tops our main list, plus one more that matters specifically for first-timers: the booking process is more transparent than most. No deposit required at booking removes the single most stressful piece of the first-time experience, which is committing money before you've actually seen anything happen.
Their customer service team is also patient with the kinds of questions experienced shippers don't ask anymore: how does pickup work, what does the driver actually need from me, what happens if I'm not home. None of those are dumb questions; they just stop getting asked once you've been through the process.