Are you sending midi from OT to Live and then send the audio into OT to sample it or are you sampling stuff that’s sequenced from something other than OT?
I sequence softsynths inside Live from my OT and sample into OT pretty much daily, no issues with that.
But as @darenager mentioned, OT is not synced to Live. I just match the tempo. One of the best things about OT is that you can easily capture loops that are perfectly in time.
If you are sequencing from within Live or from another hardware seq, I guess it would be best to put the midi notes into OT and don’t sync either OT to Live or Live to OT, but just match the tempo.
You can use live recording mode to let OT record incoming midi, but then you’d have to send start/stop from OT to Live or vice versa (or start both manually and correct the recorded midi by hand) and then switch it off for sampling.
Midi involving hardware sequencers and daws isn’t flaweless, depending on individual setups it can work well, though. Especially when you have an ERM Multiclock, Expert Sleepers USAMO or something similar.
Overbridge works very well for distributing clock and start/stop from a daw to other gear. If you have an Overbridge supported Elektron, you could use it to sync OT to your daw, but for sampling softsynths I’d just sequence from OT and match the tempo. Much, much easier and faster, because when you load more effects or use a different softsynth, latency increases or decreases. There are so many variables you don’t have to worry about when sequencing from OT.
If the midi is complex, maybe it would work to resample it in Live and then load the audio into Simpler/Sampler. Then trigger playback from OT (C3 note plays the sample at original pitch, a C3 in Live is C4 in OT? Or was it C5?), send the audio to OT and sample it. That way you won’t have to put all the microtimings, velocities etc. into OT by hand, but still have the playback synced by sending a midi note to Live.
I never tried that, just something that came to my mind…might be a good solution.