Don’t give up! What you’re doing is all doable and can be done with the flexibility and smoothness you desire. Just give yourself some time to adjust, hopefully you’ll find the workflow in good time
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To echo what others have said you should try maybe learning the device itself for a while. and build up some tracks to record and then tackle overbridge later so you’re not trying to learn both at the same time.
From your description it sounds like you’re getting your audio in correctly That’s good! The easiest way to just work with the recorded stems after you’ve tracked the dt is to mute the plugin track.
Also worth noting, Are you trying to use the DT as an audio interface at the same time? OB isn’t really meant for that workflow. It’s more for being able to connect your Elektron boxes to your system without taking up extra inputs on your actual interface.
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I don’t have much to add beyond what my fellow Elektronauts have said, however:
‘… when I go to play back the audio, the DT is still connected via MIDI so it plays itself when I use the transport controls. This has lead to all kinds of frustration’
This is still a minor irritation for me too, however it is easy to remedy - simply mute your Digitakt tracks on the hardware upon playing back your recording in Live. 
‘when I record from the DT into Ableton, it generates a blank MIDI clip. Should there be something in there that I can manipulate, or is it supposed to be blank?’
I think you’re referring to the MIDI channel in Ableton Live which hosts the Overbridge plugin - if this is record-enabled then you will generate a blank MIDI track while recording. You can try turning record arm off for this track (not sure if this would affect anything) or just disregard it.
The Digitakt was my first true Elektron experience - I was dumbfounded by it for a few days, couldn’t even figure out how to record a sequence - but now I believe it has the quickest and best-designed interface of any sequencer yet created!
Also apologies for my crude method of quotation, haven’t figured out how to block quote like the elders of this forum.
I would like to chime in with the others. Give yourself more time with the Digitakt to learn it and get a feel for it. Once you have your grasp of it, try working with Ableton and Overbridge. When you do, always make sure you have the latest compatible OSes to make sure things that should work, work. Also, a lot of us in here have had the same kind of start you’re having, so in that regard, don’t worry about it and keep trying. If you find that the Digitakt really isn’t for you, that’s ok too 
If you find yourself gravitating toward it and the Elektron workflow, you’ll probably end up getting another Elektron box to complement it. I read that you’re interested in the Digitone. You will encounter the same challenges with it as well. Its Overbridge functions are identical to the Digitakt just less tracks. It’s an awesome FM synth but it has no sample functionality if that’s what you’re looking for.
I recommend keeping your manual handy and doing some forum searches if you have any more issues.
I just want to thank everyone for the advice, encouragement, and tips. This right here is a reason why I am really starting to love Elektron’s stuff in general, as there’s a great community around it here to help me when I run into something.
I need to give the Digitakt more time. I think I’m going to separate it from my DAW and maybe get an Arturia Microfreak to make a little DAWless combo that can do everything I need. I think I get myself too wrapped up in the final product when I step into a DAW, and maybe isolating myself to hardware before even touching the DAW will let me focus on making the music first, then adding the gloss and final touches when I finally bring it into the DAW.
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If you sell the Digitakt for the Digitone you will then miss the Digitakt and buy it again. Why buy it twice? My guess is that you will have both within 6 months and be very happy
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If it helps I never think or try to bring my DT to my daw for anything besides just recording what I did and unplugging it. It’s easier and faster if I want some drum tracks in my daw to just start in the daw and use the extra tools available to me to shape it.
But in a small setup for fun and “live play” wow is it great.
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I think this is a good way to go. Plenty of good advice around here always but for sure spend some time just with the DT so you get into the standalone workflow.
It’s an incredibly fast and intuitive machine once you’ve mastered a few core functions. Dedicate an afternoon / evening and you’ll be well away.
Adding a Microfreak is also a great idea too as it will pair very well. You can easily make a ton of sounds/ samples from it (drum sounds too) and now that the DT can have it’s inputs running through the FX / mixer section you’ll be able to juice up the sounds of the MF and perform and perfect tracks (or not - depends on what you enjoy doing of course).
Either way then it’ll be a good time to hook up the DT with your DAW and explore routing and recording with OB so you can refine things later if you need to. I guess the key is to have fun and let the music happen 
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If you really like your soft synths, you can also create a more basic hybrid approach with your Digitakt and your DAW. If you set your DT as your audio interface, and monitor from it through headphones, you can use your Digitakt to sequence (and montior) a bunch of VSTs, without having to fuss with Overbridge or trying to multitrack from the DT itself.
You really can have endless fun with the DT and the Arturia V collection, and sequencing soft synths with the DT is a great way to learn the power of the MIDI sequencer. You can parameter lock per step up to 8 different CC values, per MIDI track. The Prophet VST is fun for days. I love the Solina, Farfisa…so many great toys that play so well with the DT.
Have a blast!
Sounds fun, are there any tutorials on how to set this up?
I am using a PC and Ableton 10, so not sure of any nuances that may be a bit different…but later this evening for me (I am Pacific time in the US) I’ll try to set it up as simply as possible in Ableton and share screen shots/details of how I am going about it.
I did post a ways back an approach to using Overbridge which you can check out, but for you to get started in a way that is more direct, I think it may be possible to do it more simply. If this works, let me know…otherwise I’ll see if I can’t spin up something a bit easier.
I knew I gave up too quickly. Today, I did a little experiment and just took the first 8 songs that came up on my Spotify shuffle and tried to make it into a little beat. Here’s what came about:
Honestly I’m pretty happy with it, and I’m mostly posting it here as proof that I can, in fact, make music if I try 
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@lumiras As you are into ambient stuff, check out the clip below. Patch notes and the used samples (simple guitar plucks) are in the description. This was highly inspiring for me when I got the Digitakt!
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Just had a chance to test, and it’s really straightforward to set up.
- In your DT go to SETTINGS -> SYSTEM -> USB CONFIG and check OVERBRIDGE to yes
- Open Ableton and create a new set. In preferences, under Audio, I have these settings:
That’s pretty much it, really. After that, start pulling in VST instances from your Arturia Collection, and assign them a MIDI channel:
In this case, I have a Prophet set to MIDI channel 1.
- Then, select a MIDI track (such as MIDI A) in the Digitakt, go to SRC -> CHAN and hold down FUNC and press down ENCODER A, which corresponds to CHAN and it will default to MIDI channel 1.
From there, you should now be able to monitor the Prophet VST through the DT, and also hear the DT itself through the headphones. If the gain from the VSTs is too low, you can go to SETTINGS -> AUDIO ROUTING -> USB TO MAIN [db] and increase the incoming signal by +6, +12, or +18 (default is 0).
Add as many VST’s as you like. For extra fun, go to the AMP page on the MIDI track to select MIDI CC values to control from the DT, and then back to the FLTR page to start setting values. To activate any of the 8 spaces, again FUNC + press the encoder. Then you can start tweaking and parameter locking things like filter cutoff, resonance, etc.
[edit] What’s easy about this approach is that you don’t have create any instances of Overbridge in your DAW. The Overbridge setting checked to Yes in the DT is only used here to enable it as an audio interface. Keeps things really simple!
Hope this helps!
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As was already mentioned here, working with the DT alone instead of connecting it to the PC works better in the beginning, because you learn it’s way of working without wanting to use all your known conveniences of your daw. A daw can do everything you can imagine, but the DT is limited in it’s capabilities and workflow, which isn’t a bad thing it’s just different. Take the DT, sample some sounds and play around with it, create some loops, explore trig conditions, it’s a different way of making music compared to a daw.
There is a guy on YouTube called oscillator sink, who does amazing DT videos, check him out.
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Do you really think the solution for being overwhelmed with the DT is to buy more gear to make your setup more complex?
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Removing the DAW from the equation. A single mono synth into the DT with the new updates won’t be nearly as complex as the DAW route. So I think the answer is yes since the setup will be less complex until it’s time to go to back to the DAW. No need to figure out interfaces/audio routing through OB/multiple MIDI setups/etc… just headphones, the DT, and a single mono synth.
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Just saying, the DT by itself is more than capable. Maybe work on it without the DAW? Or not, buying more gear is always fun. Just maybe counter productive if the goal is to learn how to use what you already have better.
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Amazing, that easy! Thank you so much.