So many ways to do this. One is, you can y-cord (or as many splits as you please) into your OD boxes, then mix the OD outputs with a simple line mixer, feed that into an amp or amp simulator, then onto a record track. Another way, Y-cord with one side going dry into your recorder, the other passed thru an OD box, amp or simulator, then into your recorder. Record your track, then take that dry track, send it into as many OD boxes as you want via mults (multiple Y-splits). This way you concoct your fuzzy soup after recording the track, and you can pay attention to the tones you get in the mix. Plus you already have one distorted track recorded as a reference, which you may or may not want to mix with the other sounds you develop.
If sending signal to more than one amp, sorry the best way IS via transformers, otherwise you're sure to generate ground loops with lots of hum & buzz you can do without. The good part is you don't need expensive transformers. I built a custom pedalboard 20 years ago with 5 parallel outputs to drive 5 amps. I built a quick easy buffer based on MXR MicroAmp, drove 5 cheap Mouser TL018 transformers with that, followed each transformer with a mute button, and had a very happy customer. Don't worry much about the theoretical loss of bandwidth with these transformers. The spec is given at the signal limit, and it's low end rolloff anyway which may turn out to be a blessing when driving OD & fuzz boxes. These are guitar signals, not hi fi, we don't need flat 20 Hz to 100 KHz response. Have fun! And put up some of your recordings here, or a link at least.