Hmmm... Many opinions, few data points. I did quick test: Set up a MIDI track to send 96 note events at 10-tick intervals at 960 PPQ and 100BPM (.625ms/tick). Plugged a MIDI cable from the Out to the In on my M-Audio Omnistudio USB interface, and recorded the output of the test track. No synths or controllers were involved, just MIDI data making a silent round trip.
Average round-trip delay was 11.1 ticks = 7ms. Assuming delays are equally divided between sending events and clocking them back in, that means MIDI events recorded from a manually played hardware synth might get clocked in 3.5ms (5 ticks) late on average (not including delay between the keys and the MIDI Out on the controller). Not perfect, but I can live with it.
But here's the kicker: Standard deviation of the half-a-round-trip values was 0.5ms (less than 1 tick. So "jitter" is basically a non-issue in this test.
For reference, I ran the same test with the same setup at 96PPQ, giving 96 events at 1-tick intervals. Results were about the same within the limits of the lower resolution. Mean round-trip delay was about 0.9 ticks, and half of that is .45 ticks = 2.7ms, with a standard deviation of about 1ms.
In summary, it does not appear that jitter is a significant problem in this test configuration, and higher clock rates do not have a isgnifcant impact one way or the other. This makes sense, as even 960PPQ is extremely slow compared to system clocks running in the Gigahertz range with a 1000 or more CPU cycles going by between ticks.
I will say, however, like others, that I have had more trouble with MIDI timing errors in the Windows era than with the old MPU-401 hardware interfaces with their onboard clocks running under DOS. But I have always been able to fix these problems with configuration or hardware changes. Based on that experience, and the results of this (admittedly crude) test, I would say that anyone who can actually feel/hear a significant MIDI timing issue on his/her system probably has a system-specific configuration/performance problem that is not inherent in either the OS or the application.