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So if a land speeder gets in the face of a character, for arguments sake there's a unit closer to the whirlwind than the land speeder, and the datalink stratagem is used would I be able to hit them with the whirlwind? How about if there's a LoS blocking terrain? whirlwinds don't need line of sight to fire.

The targeting characters rule from CA says :

"An enemy CHARACTER with less than 10 wounds can only be targeted if it is both visible to the firer and it is the closest enemy model to the firer. This means that if any other enemy model is closer, whether it is visible or not, then the enemy CHARACTER cannot be targeted."

You cannot target the character with the whirlwind, not even with the telemetry stratagem.