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Beautify your town (plant flowers, put out benches etc)
Buy all his available products
Do a job for him (don't accept a job you aren't sure you can complete - as this will set back the relationship level if you fail the task)
Chat to him.
https://steamuserimages-a.akamaihd.net/ugc/1917988143676386179/AED8E0AD05623D13CB22731CC58947DA5BE09665/?imw=5000&imh=5000&ima=fit&impolicy=Letterbox&imcolor=%23000000&letterbox=false
Either he is bugged, or there's some RNG involved with when someone joins a town.
Maybe you need to fulfil some other criteria to get him to join. Maybe some of the categories (business, commodities etc) has to be at a certain value. Is one of them especially low compared to the others?
That's a good question. You can check that with Fletch, right? I had that option for many days, but I can't find it anymore... so I can't check what levels my town is at. So I do think my game is bugged in some ways :-)
https://steamcommunity.com/sharedfiles/filedetails/?id=2838690373
Oh wow, could have sworn it was also a chat option.
https://steamcommunity.com/sharedfiles/filedetails/?id=2838695716