Agreed about Buffalo. The Jays having to play there in 2021 could definitely factor into how successful they can be in signing free agents. There's no guarantee that they'll be allowed to play in Canada by the start of next season, so convincing a (good) FA to sign with a team that might have to play in a minor league park some/most/all season could be difficult. Plus, if there is a minor league season, how do you juggle the AAA affiliate in Buffalo with the Jays having to play there? Unless the Jays play in Dunedin instead. Lots of uncertainty there. Of course, money talks.
Anderson's option should not be picked up. As mentioned, there will probably be a slow free agent market after Covid, so $9m for someone like him would be absurd. Pay the buyout, and get someone better. Roark should be dumped, but don't think he will be. Over a 162 game season when he doesn't have to pitch against all East teams, he might go from awful to just bad. Plus the money isn't going anywhere, they have to pay him anyway, so unless he's traded for a worse contract belonging to a more useful player, they probably hold on to him.
I've said before I think there's going to be a s*** ton of non tenders this winter. I wouldn't make any unnecessary financial commitment until I know what's available. The supply is most likely going to exceed the demand. That's where the Jays can really take advantage (assuming Rogers will spend).