My experience with scraping is that if you aren't doing anything super complex (like logging into a secure website like an online banking website, etc.) then Python has some great libraries that will help you out a lot.
To answer your questions:
1) You may need to be more clear, but this really depends on your server/client architecture.
2) As a matter of fact you do. Urllib and Urllib2 (built-in Python libraries) both have functions that enable you to encrypt data before you make a POST. As far as how secure this encryption is, for most applications, this will suffice.
3) I actually have done scraping on online banking sites! I'm not exactly familiar with that tool, but I would recommend using something a little different than a scraper. Selenium, which is a "web-driver", allows you to simulate the use of a browser, meaning anything that the broswer does in the background in order to validate the session is automatically taken care of. The main problem I ran into while trying to scrape the banking site was the loss of important session data.
Selenium - https://pypi.python.org/pypi/selenium
Other libraries you may find useful are: urllib, urllib2, and Mechanize
I hope I was somewhat helpful!