What's the difference between 'on' and 'later', 'if' and 'though' in the following passage? Thanks.
Two years (ON/LATER) from redundancy, Caroline is planning another career break . “ The experience of redundancy has made me view my options with more confidence. I now know that I can dictate my own career path, even (IF/THOUGH) it were to mean resigning first and then taking time to find the right direction” she says.

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David, you would structure the sentences differently.
1. If you had already mentioned redundancy, you would say, two years later, Caroline is planning....etc
You could also then use' two years on' in the same way - 'Redundancy.... Two years later, .....' etc.

Otherwise, you could say 'two years after redundancy....'

2. 'Even if'... takes 'it were to mean...'  This is more uncertain, and conditional. 
'Even though' takes 'it could mean resigning first....'  This is if you want to retain the uncertainty of the following phrase.