It’s possible to overdub with flex, even clock slaved, but it’s better easier with pickups I think (master clock only).
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Here’s how I set up Flex Machines for looping:
track 1 has a flex machine using recorder buffer 1 for playback
Hit record button and enter a regular trig on step one so it plays the empty record buffer
While still in record hit Function+AB to bring up recording options for the same track/machine
Hold function while you enter another trig, making a one shot recorder trig
That’s it.
I use a midi controller to enter the CC for arming the one shot during playback, essentially remotely pushing the Yes button.
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That’s how I was doing, but I think I’ll use pickups for monitoring and track fx reasons.
I use other traks to mangle the recording.
Do you prefer Flex?
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I prefer flex when I’m sampling into OT and I’m following its clock, or whatever is driving OT as a MIDI master. I use pickup machines when I want OT to follow me, and adjust its clock to whatever I’m playing.
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More detail here
1/384 offset is required on play track trigger as explained here
The offset isn’t required for @stonecoldgroove’s setup he described…
But that is not what OP is looking for since they want to overdub. For overdub using src3 set to cue, you then would want the 1 notch of micrtiming forward on the play trig… (Edit: this creates feedback)
Live inputs: no micro timing adjustment needed
Any Src3 setting other than “-”: 1 notch microtiming forward for play trig
Edit: Above is for live monitoring inputs or tracks but not nessecarily overdub
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Maybe I have a special OT, but to I have never had to micro-time a trig to get it to work for me.
Granted, I’ve messed with the micro-timing ( for this topic purpose) very little, and I’m not trying to monitor what I’m playing as I sample it: at this point, I only want the sample I’m making to be heard after I’ve played it and the sequence restarts.
This is with recorder trig and playback trig on the exact same step.
I experimented with micro-timing the playback trig to attempt overdubbing on the same flex… this resulted in feedback, so that particular experiment has been shelved for the future.
Ahhh… so if I understand you, overdubbing on the same flex requires sending its output to Cue and overdubbing with the +1 micro-timed playback trig?
I guess there’s a few ways to do it with flex, I usually just use pickups for overdub…
One way is set Src3 to the track playing the loop you want to overdub onto, and also select the inputs on the same recorder…
Another way is to set Src3 to cue and then simply cue the tracks you wish to combine together, or also select the inputs to overdub on top of a cued track or tracks…
In either situation if you want to monitor the new track as the overdub is happening, you would need the microtiming offset. It will still overdub without microtiming but you won’t hear the recording until after its done…
(Edit: the microtiming trick creates a feedback loop if trying to overdub on one track with flex)
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I succeeded to overdub with Flex, OT clock slaved, because somebody asked and was surprised to have the DUB ARBORTED message with Pickups, clock slaved.
Quite boring, since I can achieve what I want with a Pickup with QREC and monitoring instead of Thru + Flex. OT master.
Already too much gear, but I still think about my former dedicated loopers, sooo simple ! 
Yeah for realtime monitoring with SRC3 you need +1 microtiming but with Flex overdub you get an awfull feedback if I remember well…
So there’s a monitoring problem if you want to hear track fx in realtime. Resolved with Pickups.
I want to try hold mode combined with recorder trig to see if you can press different input selections at the same time, for overdub… 
And then mix and match them… I guess if it works it would be similar to Src3 cue, but a little different…
Could you elaborate?
I used hold mode once, in a complicated experiment, something like Plays Free tracks playing recordings, Plays Free midi tracks controlling recorders in hold mode… 
From @dustmotes idea !
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I’m talking about recording hold mode as opposed to one or one2…
If you set a recorder trig and combine with hold mode for a 64 step recording, after recording begins if you press track+a/b for 32 steps and then track+midi for 32 steps, your recording is 32 steps of a/b inputs then 32 steps of your Src3 selection.
I don’t know if you can press track+midi+a/b at the same time, and then let go of a/b and press c/d…
So that you’d overdub a/b onto half of the recording and c/d to the other half, for example…
With Src3 cue you can do similar things by changing what’s cued during recording, but this would give you direct input access and not need a track that’s monitoring inputs to cue…
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Video tutorial ?
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I kind of like to keep pushing the envelope without necessarily implying or even knowing why or what you’d do with it…
Push envelope first, see what’s possible, then figure out what to do with it… 
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Right, I can see how a track playing a recording of itself as its recording is a feedback loop… 
I don’t know if I’ll figure it out without the OT in front of me… Use 2 tracks? Just don’t live monitor that track? Other stuff? I’ll maybe edit my post above to not confuse, and post back if I figure something out…
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Yeah, but surprisingly there’s no larsen feedback without microtiming, because the recording is delayed…
I just made some tests, a recorder recording its recording, and you can obtain crazy things with filter self oscillation. It works with or without microtiming, but beware with microtiming !
I thought this was figured out before… And folks said you could use one track?
Just using a different recorder than the track # set in Src3 will resolve the feedback loop, but uses another track…
If your loop you want to overdub onto is track 2, using any other recorder besides recorder 2 won’t create feedback.