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I'm not clear on how your tailscale names are attached to the services. Do you mean you've got a different Tailscale magic DNS for each docker container with a sidecar?
I'm not a Tailscale expert, all my services are in VM's or LXC's so they get their own Tailscale name that moves with them. Perhaps Tailscale allows you to add extra names for the same host or something?
I've got few docker containered Tailscale deamons as a sidecar, exactly. Those should work as the same host (login based), as in the original home server. I'm mostly unsure, how the whole "VM environment" with attached drive with whole docker engine install will perform - also in terms of connection.
So their names would come across with them. In what I'm proposing, you wouldn't worry about attaching the drive. Just copy the data for one service over, then start it's container on the laptop. Once that's all working fine, do the rest one at a time till they're all on the laptop. Then wipe your Dell and start from scratch.