Will there be a way to influence the rolls with clever roleplaying?

In Max's example, the options are to wait until morning or break into a building during the night. If a player sends a ghost pokemon to float through the wall and unlock a door, or a teleporting Abra to do the same, or opens the lock with a Klefki, will it add a bonus to the roll?

What roll would it be, anyway?

If the roll check is failed and the team is caught, can they then also make a Con Artist roll to talk their ways out of the situation (or roleplay for a similar result)?

Will the chance for a roll always be presented as A or B, as in your example? As in, will we always have the choice whether or not to take an action that will lead to a roll? Or are rolls secret and inescapable?