1911 makes all the difference- think I found him!!!
Only one Checkett (thank goodness for an uncommon name) in Canada at time of 1911 Census (on automatedgenealogy):
James Checkett age 14 servant born Feb.1897 living at Amaranth, Dufferin, Ontario.
If you click split view on census result page you can see scanned original: James was a farm labourer, born England, Methodist, and came to Canada in 1907.
Seems his date of birth was also wrong. Now you can go back to passengers lists with the correct age and see if he's there going to Canada in 1907.
There might be someone in Ontario who can find more details now that a place has been found.