So, I’ve been thinking about this for the last year, and am still torn. I normally don’t go for this but…
I can only have two. Opinions? Reasons (I have thoughts)
Keep in mind I have Peak, Octatrack, MPC Live
Thanks in advance
Side note: i put up a bunch of other stuff for sale too
UW? If so, do you prefer sampling on it compared to DT? Regardless, judging it only by the crazy second hand prices for the silver boxes (and the fact that you can always re-buy the Digis whenever), isn’t the choice pretty obvious?
UW…yes.
Ya I know the oldies are irreplaceable. The choice is obvious. But I still struggle.
Well you’ve got Octatrack
So you only need 1.
I would get digitone. Because I have one and its proper.
Why make the choice anyway? Space? Cash? I’d say DN is still pretty special, but maybe the DT can go because MPC, OT and MD UW has you more than covered for sampling.
I would choose Rytm and Digitone lol (in this case maybe the Machinedrum but I lack experience with it).
Oh no…I’m not acquiring anything. I have all these already. I can’t anymore.
Low on money, space and talent. I really can’t justify all the gear I have.
So I’m trying to decide what to sell.
I had A4 and Rytm…sold those.
Pairing down. Keeping it light, simple and trying to recoup some money in tuff times.
I think this answers itself no? You either really dig the classics, and how polished they are; or you are into the new boxes and all that entails.
Considering the other gear that you have, I would go for keeping the Machinedrum and the Monomachine; as you get the best digital drum machine ever made; and an interesting sequenced synth.
Octatrack covers all what the Digitakt does; and Digitone… well… do you dig the tone? More/less then the MonoMachine?
Me: Love Machinedrum. Hate Monomachine. Never used a Digitakt or Digitone.
Are you me? Am I you?
Tough choice, all great machines. If only choosing two, I would keep the Digitone and Monomachine. And before you sell the Machinedrum, sample it with the OT or MPC, and keep a library of your favorite sounds from it.
But I also agree that the silver boxes are worth holding on to.
Tough choices for sure.
I’d keep the digitone and the Monomachine. Digitakt feels the most redundant with the other gear you have.
Oh! You’re selling!
Well in that case its easy.
Pick your favourite 1 Synth, 1 Sampler and 1 Drum Machine.
Sell everything else.
Sample the gear you think you will miss before selling. Simple.
Easy formula. But then I factor in midi possibilities/disadvantages, audio routing +/-, trigs, UI…
Example: trig conditions…love em. Use them?..not as often as I thought I might. But they sure can be handy.
Thanks for input tho.
That goes for everyone.
Digitakt and Digitone, obviously.
Don’t even worry about posting an ad for the MnM/MD. Just message me directly and I’ll save you the hassle of having to worry about selling it. 
I have only DT and MnM from your list - I’ve been thinking I want Octatrack mkII and the 2 silver boxes over the past year so I’d keep your silver boxes!
Of course you’ll make more space and money selling them but if you regret it later it won’t be easy buying them again - plus you might be even more out of pocket at that point as they are not getting any cheaper.
EDIT : I’d keep the silver boxes not because of their value… but because they are just awesome.
I would personally go for MD + DN.
Digitakt is IMO redondant with OT/MPC.
Monomachine is unique, but I find it less appealing than Digitone, these days.
My main use of MM is FM (I find it easier to dial what I have in mind with DN) and retrigs on drums (for which OT is better).
MM arp is still something special, but nothing OT MIDI can’t do.
Thing I miss most on MM is saving Sounds for later reuse.
I’d say don’t hesitate to raise the price for this one, you’ll be less worried to let it go: after all, it is special.
Machinedrum is still very special, to me. I just can’t get enough of it.
Where MM filters are hard to tame, MD ones are pretty funky. And these LFOs that you can assign anywhere. And resampling…
And who needs Sounds on MD? It’s so quick to reach decent beats with this machine!
Maybe try different pairs for a week each, then decide with which pair you had most fun and stick with those.
I know there are many logical arguments that would justify a pair over the others, but there are arguments for every combination so you should just go with what gives you the most pleasure, because ultimately, this is what’s gonna make you come back to them and play more often.
Personally I would probably keep the OT, DT and peak and sell everything else, but I do struggle with more than a handful of pieces of gear personally.
But with those 3 you would have everything I would need lol!
I love this, it describes me perfectly. 
Two DN’s, one for drums and one for melodic/noise content, sell the other three and buy a motorcycle or something.