I think your calculations are very realistic and you won't have a problem to live in Crete.
I will add some comments here that may be useful to you:
1. Crete is not a cheap place to live. it is very hard for a couple to make it here with less than 2000 Euro per month. This amount includes the rent for a descent apartment as well.
2. The prices for apartments vary greatly according to the location of the house, whether it is in or out of a city, how old it is, view, etc. For a 2 bedrooms apartment wit central heating inside a city like Heraklion, you should expect no less than 400 Euro per month, but prices can go up to 800 Euro per month for something special (sea view, parking. new building).
3. There is a lot of offer for English teachers and the fees are rather low. For example, a friend used to work part-time (20 hours per week) as an English teacher and his fee was 400 Euro per month plus social insurance (this is important).
4. For web-design there is a lot of competition too. I am in this business so I know about it first-hand. You may find a few clients, but don't expect much.
Moving To Crete
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