Interesting. I kind of replied to the first line in an edit above, but the second one intrigues me.
Probably this just proves that my accent is crap, but for me 'then' and 'than' sound about ~the same~, ditto for 'their'/'there' and 'loose'/'lose'. Again - probably I'm just missing something here. Improving my spoken English is definitely on the list of things I want to do..
I don't think it's a question of sound. (I'm french)
'they're', 'their' and 'there' sound the same (spoken or in my head), but their meaning has nothing in common so I never mistake one for another.
How you acquire a language plays here. I learned english fully conscious of what I was doing rather than my organic absorption of french.
In my head, "then" and "than" sound totally different. Same with "they're", "their", and "there", "loose" and "lose", etc.