There is a problem, that is an edge-case, when using SS2 and Transfer Settlements on a new game. SS2 always triggers the main quest after you build your first recruitment beacon. If you build your first settlement by importing a Transfer Settlements blueprint that has a recruitment beacon in the blueprint, then Jake will show up before the import is finished but you will never be able to initiate dialogue with him.
The fix was to first build a recruitment beacon and generator to trigger the main quest. Once you've had the dialogue with Jake, you can import the settlement. Just don't talk to him again or build anything until you have spent a few days far away from the newly imported settlement.
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