Yeah I've liked Web since day one. Reason I like him is he's a smart player. The guy never looked confused lining up, had sure hands and seemed to be in the right spot, and he was a teams addition too. He'll be tough to knock off the roster in that wideout group for those reasons.
Kupp, Woody, JRey, and Jefferson are locks (barring something like a trade). So the competition will be 1 or 2 spots. Here's the chart as I see it at least:
Kupp (big possession option)
Woody (swiss army knife)
JRey (highpoint and redzone type wideout)
Jefferson (big possession option)
----------------------
Web (smart depth who helps on teams)
Jackson / Edwards / Koski / Winston
Of those bottom end options having return ability is going to matter IMO. That means I'd favor Edwards and Jackson for that final spot. Koski can do that btw but he's going to look like Web doing it (not a lot of wiggle).