So I'm super late to the party, but here are some thoughts now that we know Augie is the person we're contacting.
I think asking about Tinkerdown could be a good way to learn about our limitations with this time magiq. Is Augie the only person we can talk to? Will we be able to speak to people like Tinkerdown directly, or at least use Augie to reach out to others?
The other thing is considering why we're being sent back to this moment in time, and why are we speaking to Augie specifically? I feel like we should assume the events of the past are set - we won't be able to do something like stop the Storm from coming for the '94 Mounties. So...what does that mean? Maybe we're meant to help Augie in some way, but how, and how would that affect our current situation with the Book of Briars? Maybe learning about the past can help us track down surviving members of the Mountaineers? Or perhaps we can get in touch with Fletcher Dawson, figure out who they are and how they're connected to the Book?
I'm sure we'll figure this out the more we talk with Augie and reach out into the past, but I think we should definitely try to figure out what our goals are in this endeavor, so we can orient our questions towards them. Especially if we have a limited number of messages we can send before we lose the connection.