you should check out this site
http://anglish.wikia.com/wiki/Headside
Anglish is a project that replaces romance language words with anglo saxon based ones
Hamlet's famous speech becomes:
To be, or not to be – that is the asking:
Whether ‘tis worthier in the mind to bear
The slings and arrows of unbound mishap
Or to take fight against a sea of worries
And by gainstanding end them. To die, to sleep –
No more – and by a sleep to say we end
The heartache, and the thousand worldly blows
That flesh is born to. ‘Tis an ending
Dearly to be wished.
Another question is whether the great vowel shift would have happened - One theory is that this was a consequence of social mobility after the black death,
If the higher social groups had continued to speak English the social mixing after the black death might not have caused such a change in pronounciations and spellings