Yes mate, I have spent lots of time playing with different quantize settings and I like the way it’s similar to ableton in that respect.
It’s fine if all you want is two and four bar loops. Solid.
That’s a false dilemma. There’s a plethora of possibilities between playing “live and in realtime” and the playback of a complete track. As to the appropriateness of the gear for such usages, as always, YMMV. Personaly, I’m fine playing a complete set with the DTakt’s 64MB… but the Blackbox streaming offers other very interesting possibilities. OP did mention long loops.
Again, that’s a possibility and there are others. Some of us conceive their live sets (or even albums) as a continuous flow. It’s not about paranoïa, more an artistical choice.
There’s more than on way to do it 
Yes it does, with accuracy and ease, even with very long loops (64/128 bars), even when changing the tempo, that’s why I’m surprised it’s not working for OP.
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Fair enough. Just giving the OP some food for thought…
Cheers!
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Second octatrack
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Nobody has mentioned thr new roland or the electribes.
Not having used either, or looked into them, are they of note?
I don’t remember exactly but when I used bitbox like this it had very good sync for long loops. I think I had to adjust the setting in sync to longer values though. Maybe the same applies to Black Box
Syncing very(!) long clips on BB is super easy if you keep your clips exactly 2^n bars long. You can go up to 4096 bars. Check the 1010 forum or the BB thread in this forum.
My loops are between 64 and 128 bars long and time stretch no problem. It even handles pitch changes with time stretch quite well, at least when you pitch them down. Up, there’s artifacts that at least I don’t like.
Yes 
i had been interested in the BB for a while as i thought it would do exactly as you’re describing OP. glad i havent pulled the trigger on it yet!
also thought about using an MPC500 for the task, but i imagine the time stretching doesn’t work that well?
It really does time stretch quite well, to external sync as well.
You mentioned iPad. Beatmaker 3 does time-stretching, sampling, chopping, and triggering.
In short: No.
Electribe sampler is 24MB, also no timestretch, only slicing. Not a great fit for long loops.
MC-707 has stupid limitations regarding the looper (very short memory for the entire project). Also, very slow card access/browsing. Oh, and bugs. Many. Bad ones.
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the MPC500 or BB?
The BBox.