I think the way to go is to add a useful player or two on expiring contracts. If things don’t work out, trade them at the deadline in a deal for Barnes, Collins or whoever else might be available.
This is how I see it too - go get a bench vet making low teens who can soak up some December/January wear-and-tear on the Jays, even if it you have to ship out Nesmith to do it. If they work out really well then great, and if not you can really easily staple together a few contacts with as many firsts as necessary to get involved in talks if a big name guy comes available.
Like, he's not going to excite anyone, but Terrence Ross can give you 15 minutes a night against Charlotte in the middle of the winter when guys are dinged up, and Ross/Theis are about $20 million in contracts to play with at the deadline.