Hello nihal,
Recently i've been automating a few tests in my company and gladly they set me free to do as I found more suitable. I've chosen python, selenium and behave (BDD testing).
I learned that we might face problems like 500 - Internal error, how would you handle it?
Also, in Internet Explorer, sometimes the page is loaded with success yet the button refuses to be clicked, how would you implement a retry - if that's the approach? How would you capture the error?
A few days back, I learned that some problems I was facing could be solved cleaning cookies, had to go after it.
My two cents for you is, try to automate a really bad designed website. You'll have to learn a lot of things about selenium AND python and will have to implement a few new things here and there.
Depending on your implementation, you might have a challenging task ahead.
GL