Not sure I can follow your calculation. If the iPad is (at most) $800 and the MacBook Air is ~$1800, you'll save roughly $1000 if you go with the iPad. If a cloud server is $20/month than it takes you about 4 years to spend these $1000. Thus if you compare the values within a time span of 2 years, shouldn't the iPad+server combo safe you roughly $500?!
I'm sure I'm missing something.