You can add 4 individual outputs to the A4! I did it, though I ended up selling it to @DonovanDwyer.
My 2 boxes would probably be the DN and OT. Synthesis and sampling in a nice little pair!
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All my 2018-2019 shows were with the OT/MD pairing, loved it.
If we ever get back to it, I’m thinking OT/Rytm is the new pairing, to take advantage of the Rytm dual VCO.
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MnM and MD for me. Its the way they sound and their quirky nature.
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A4 + AR. Mk 2 for both.
I only have two elektron boxes but for me having a digital and analogue groovebox in the DN and A4 MKI feels very powerful. Still very much in discovery mode with both.
I’ve got my DT paired with my DN. Works well for the stuff I’m doing. Looking to pair my AR with my A4, and see how that works for out for me.
I’ve been using Octatrack + Digitone, mostly because those those are the only ones I have, but that comes down to them being the only ones I’m deeply interested in besides the monomachine. I’m actually using this combo to approximate a MnM, with the digi’s FM and using the octa for various sample-as-oscillator synthesis methods as well as a convenient place to have vocal tracks.
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The A4 MKII and AR MKII, as they are the two flagship Elektron products that I presently own. I also have the Model:Cycles and Model:Samples in my collection, but do not prefer them over the former two options.
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Analog Rytm
Digitakt
Rytm is the most inspiring and favorite sounding drum machine (and sampler) I’ve ever had. Using Digitakt mostly for sampling my synths, love the sound quality. Due to the similar workflow on these 2, making music is a breeze for me recently.
My feeling for A4 + AR: Great couple … but Elektron has always such weird design decisions.
For example: Why does the A4 does not have a compressor for sidechain ducking (or something similar) … but the AR has one - but one that is inferior to the Digitakt (you can choose the input and even the UI is more compelling) … the Digis excell the Analogs in so many ways: I’m asking myself … WHY? Seems to me they don’t talk inhouse too much. More unification instead of making it artificially differently. Seems like they just want us to test ALL of their ideas (look at the Model series which is from usability standpoint a mixture of everything).
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To me, the design choices around the AR’s compressor seem pretty clear. The compressor sits over the drum buss, and so it’s most common roles will be glue, tone and transient control. You don’t often duck a whole drum track. The 2VCOs were added later, after the hardware design. Ducking one of the channels (e.g. a bassline) requires moving the compressor from the drum buss to the bass track, and routing any of the other 8 tracks to the sidechain input. Easy in software, harder in analog.
IIUC, the Digi is all digital. Routing happens in software. It’s much easier to offer more flexible signal paths.
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I don’t wanna discuss this in detail … it is how it is… but the Analogs are all digital in the end (otherwise we wouldn’t have Overbridge or resampling). And I don’t know … my criticism was more for the lacking option in the Analog 4 / Digitone (and I would be happy with a fake ducking function – using LFOs / P-Locks is not an option imho – I would want a function which I could tell: Use this input and then duck track 2 for example).
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Trinity! Octatrack as Master -> MIDI Hub -> Elektron devices and other gear.
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Monomachine + Digitakt for me.
MNM’s lofi weirdness mixed with DT’s clean punch sound so good together.
That’s like a shameless off-topic plug 
… I like that video though.
3 elektron pairs in my setup.
OT+MD… glued together forever. They have become one instrument which have generating so many ideas, and for performing, simply the best. I tried more than once swapping out the MD for the Rytm but it just doesn’t have the same specific set of features. Having two machines which can creatively resample themselves and each other makes song transitions alone a thing of rare beauty.
The other two are a Rytm+MM and MD+A4. Something special comes from mixing Elektrons digital and analog sources. Both pairs are missing an Octatrack though, so will always be at a disadvantage in performance, if not in sound quality.
There is also a Heat currently hooked up to an Analog Keys which sounds beef, but simply not flexible enough to be in the first two paragraphs. Haven’t really cared to try the Digitakt/tone or Model:s, but no doubt they’re capable if not ‘as’ capable in most ways that count.
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It would be tough to live without 2 octatracks…
but if I could only pick two
I’d probably go Octatrack and Monomachine
or Octatrack and Machinedrum
Tough choice. Maybe after the new firmware, Octa and Machinedrum…
I’ve owned a DT and OT. Here’s what I would want if I had to 
For versatile jamming: DNK and AR
For performing/versatility: DNK and OT
For meditative loops: DN(K) and DT
The one Elektron product I’m considering buying at some point is the Digitone 
OT + DN for me. Really having a hard time shaking the urge to put a DT on the other side. Why is that symmetry so damn appealing.
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MD mkii UW+ and MnM SFX60+
…but if I could only have one OT!