I don't see England begin colonisation process on 1490's. Tudors had too much domestic worries that it could try to create colonial empire. Henry VII's claim for throne wasn't very strong (him had only drop royal blood on his veins) and there was still Yorkist claimants. Even Henry VIII had same problems. And Scots and French were problems for England.
Well, if he's read any history, a fantastic way to deal with rebellious nobles is to send them to the ass-end of nowhere where they are dependent on you for survival, and are no threat.
Yorkists suddently find themselves leading American colonies?
He'd have a lot of money if he had the sense NOT to waste it all on invading France and getting betrayed by Maximilian.
Now could England/Britain/whatevs colonise? sure. Fishing isn't always a bad idea, although the British Isles are already surrounded. Anyone familiar with what else was in the Newfoundland area that a King would like (it would be useful to encourage further expeditions) - This is a crucial step to overcome.
Go far enough south to find Furs? Fantastic, who needs Russian furs now?
Go further to find Tobacco? Hello Tobacco Plantations
Go further to find good sugar growing land? If the English can start growing some, then that is going to be VERY profitable.
To be honest, get to Furs, and you'll already have enough reason to create a serious of resource colonies/trading posts. If they aren't obsessed with Gold (which a colonial expedition that isn't inspired by stories of Spanish gold isn't likely to be) then chances are you'll have trading posts galore, and lots of money for British coffers. If that grows enough and cultures like the Caddo don't die out from disease, then unless someone else from Europe comes along, we could see trading colonies, followed by settler colonies.