There's no sense blocking Robertson in October when adding middle 6 scoring depth for a 1st plus junk is so easy in February.
Kane, Toews, O'Reilly, Tarasenko, Miller, JVR, Pastrnak, Monahan, Okposo, Horvat, Bertuzzi, Paveslki, Barbashev, Killorn and a ton more wingers in the 15-20 goal range last season are expiring, and a big bunch of those are on non playoff or bubble teams at best.
You don't need your roster sorted by October, you need it sorted by April. Play Robertson, play Steeves (or whoever wins that spot) and if you need to make adds later, make adds later. That's the core benefit of having the Core 4 and a sorted blueline. You can take some chances on young guys filling the support roles.