I've had issues in the past, but I no longer sequence midi from my Daw. I use hardware synced to my daw using usamo.

Some amount of latency is unavoidable. Even with expert sleepers or inner clock stuff. It takes time to send a MIDI message, your synth to receive it, process it and send audio back to your daw + you have asio buffer time on top of that.

I use track delay to compensate for latency.
Are you sure it s latency and not jitter your finding annoying?

It's both. In particular latency is what's most annoying when realtime playing on MIDI keyboard to the computers DAW, but some notes will lag more than others, so I guess it's jitter too.

I have 7ms latency with low buffer settings and little else going on in a project, and It's somehow workable for a while, but gets worse as soon as the project develops, as I'll have to increase the buffer size to avoid clicks and pops.

Are all your synths and fx ITB or are you also using hardware ?
Sounds like your adding plug ins that introduce latency. You can’t have delay(latency) and no delay both at the same time.
Try using zero/low latency plug ins untill you have all your parts recorded and then swap them for the plugins causing latency.
You can also bounce/freeze tracks as you go. Once bounced remove any plug ins causing latency.

Mostly using Reason alone. Have found ways of getting around it somehow, but it's far from ideal. Main reason I bought an MPC4000., which is very tight if not overloaded with MIDI events.

This is tight...what I think it really is though is it has character. My old Mpc's that run at 96ppq sound much tighter than Logic prox running at 960ppq..what is the parts per quarter note on that version of cubase? Also..yes serial midi is better sounding than usb for sure.

Sorry to necro this but I'm embarking on a similar project.

Can I confirm that basic (ie, MIDI CC) automation was possible in Cubase 2.8? If so, were there any limitations on the number of parameters able to automated simultaneously?

You can choose between 96, 192 and 384ppqn. And there's a system granularity param that was useful for "slow" computers (read : 386 vs 486).

http://oldschooldaw.com/forums/index.php?topic=1294.0

You can record and edit CC at will, but AFAIK there's no CC "automation" or realtime processing per see.
There are some programmable tools able to generate MIDI events though: IPS comes to mind.
And it can import/export files in SMF format, so one is able to go back and forth different sequencers.

Check out these tutorials:
https://www.youtube.com/watch?v=PHqdc6L2ztg
https://www.youtube.com/watch?v=D6-DB9LFahA
VST5 had a very poor timing, but the MIDI editors are basically a port of the previous MIDI only versions, untouched.

It had a few extra MIDI processor as well not found in the older releases, but Cubase SX/SL had much powerful MIDI tools, and it can run on a current x64 OS, provided you have an eLicenser USB dongle.
Not as tight as v2.8/3.05 on a retrocomputer combo, but usable.

Great, thanks for those links. I only found SX3 videos so these are much better. I'll watch them now.

Re the automation: adds a little bit more complexity to my plan but that's half the fun

FWIW, I've been pleasantly surprised by the Steinberg Midex8 when used with a LTB compatible sequencer on an old USB equiped retrocomputer.
Much tighter than the parallel MIDI interface that is also connected to the same Win98SE/ME computer with Cubase VST5.

2 to 5 time more accurate on MIDI clock: 0.6-1.0% jitter vs up to 5%.

So much for USB not being tight.

I posted this at http://www.oldschooldaw.com too, but it seems the site is down at the moment. Would be a pity if it disappears

Iam interested in buying a modern midi interface to control my external synths with cubase as the main environment.

Which interfaces have the best latency-jitter specs? Is esi mu8ex really superior due to the usb3 connection?
Is there any shootout that i can check out?

Is there any difference with mioxl and other midi over ethernet interfaces?