This seems to be the most recent thread with this bug, so I'll bump it with a solution.
I'm using Magnum Opus, an enormous modpack with Sim Settlements 2 and a few SS2 addons.
It's using SS2 version 1.1.0a, from 8/8/21 (the latest version is 1.1.0b (which came out a day later), but the change log only mentions fixing a graphical issue with Jake's pistol, so this solution should still work.
I've checked YouTube, and on "Who can? ASAM!", after picking who should be mayor, you can sleep a few hours, then fast travel to the settlement, the bunch of settlers will be around the workbench and a cutscene starts.
With this bug, the settlers show up, but talking to them just gives options for small talk / trading equipment. I'd tried different mayors, different settlements, put resources into the Workbench, claimed a fresh spot and not touched the workbench, walking with the settlers, waiting (in game and real life), many other things, all failed to trigger the quest.
The short version for people who have played Sim Settlements 2 before:
Get 20 ASAM's, build a City Planners Desk in the new place, pick a city plan, and type setstage ss2_sirick_mq13 160 in the console. That'll complete the quest and let the next one start.
Use the City Manager 2078 Holotape, choose Tools - Cheats - Quest Skipping - Force Complete Current Main Quest.
And the full version for people like me who've only just started learning Sim Settlements 2 and want to complete the quest in as near to the proper way as possible:
Jake gives you "Box of ASAM sensors for Hubert", but when the quest bugs you can't use them, so you'll need to provide 20 of your own, you can craft them at the City Planners Desk. You'll also need some spare junk (you'll need to build a new City Planners Desk later).
I tested this with Stodge at Outpost Zimonja and Red Rocket.
After selecting the mayor and settlement, wait a day, then fast travel to your new settlement.
Everyone will be hanging around the workbench ignoring you, if they aren't there yet, wait another day.
Build a City Planners Desk.
Enter Workshop mode (where you place items), select Stodge, then select the City Planners Desk to assign him.
Activate the blueprint on the desk (not the computer or lower part of the desk, the actual blueprints on the top of the desk).
Select City Plan - I picked the Basic version by FanciestMoon. Be aware of the Triangle of Death around Sanctuary / Red Rocked / Abernathy Farm, the areas are close enough that sometimes all 3 have to be loaded at once, which can cause problems, so keep the build basic if you're in that area.
Select "Tear it all down".
You'll be given a flyby of the settlement, it looks really impressive, but is very resource hungry. You can exit the flyby by bringing up your Pipboy and putting it away again. If the flyby causes crashes, then repeat and exit the flyby quickly.
The plots will build very slowly. Putting junk in the workbench speeds things up, or you can donate it with the small safe at the top of the bottom left of the City Planners Desk. When the build is finished, you may need to check that power is connected properly to all the buildings.
You don't need to wait for everything to be build, when you want to complete the quest, use the computer on the City Manager desk, choose Tools - Cheats - Quest Skipping - Force Complete Current Main Quest.
That will complete the quest, then shortly after you'll get another radio broadcast from Jake starting the next quest.
It's the first SS2 bug I've found, really enjoying the mod.
Optionally, you can add 20 extra ASAM's by using the console.
Bring up the console (usually the key below escape, but
varies internationally)
Type
help "sensor 2077" 4
On my setup it shows:
M8r Profile 1 LVLI MISC.esp MISC: SS2_ASAM_Sensor (XX010A23) ...
The bit in bold is the item id, the XX will depend on your mod setup.
Then type in the console
additem XX010A23 20 (replace the XX010A23 with whatever item id appeared for you, it's in hex, so any 0's will be zero's, not the letter O).
edit: thanks to msalaba for clearing up some console stuff