I think Jaylen's going to take the gamble even if he doesn't make All-NBA this year. The C's can offer more, but still, there's a 100M difference between not making it and making it, whereas there's only about a 30M difference if it's between Boston or another team.
I don't think the 30M will matter much IF Jaylen really sours on Boston after next season and thinks there's a better opportunity elsewhere.
Now it's still better for us that we can now offer more than other teams outright, but we still probably need to hope Jaylen makes 3rd team All-NBA. If he goes, I predict he'll sign the 5/290M extension this offseason (if offered by the C's)