I moved from Austin, TX to Victoria, BC (still on work permit). To me, your simple plan seems nigh unachievable. From the Canadian government's point of view, what you have proposed sounds like taking a lot more than you give.
From the CIC website: "If you plan to stay longer than six months or intend to work in Canada, you may be considered a temporary worker and have to apply for a work permit." Self-employment wouldn't be an option for a work permit, even though software developers kind of fall into the skilled worker class (which helps with some bits but is a very long shot for you to bank on); you'd almost certainly need to be working full-time, and your employer needs to file for a Labour Market Opinion (LMO) to justify hiring you, which can take some time.
If you have further questions, email me at http://scr.im/amh.
ADD: Skilled worker info that I dug up.
"As of July 1, 2012, CIC will temporarily stop accepting applications for the Federal Skilled Worker Program (FSWP). This temporary pause does not apply to those with a qualifying job offer or applying under the PhD stream. We will likely start accepting applications again when the revised FSWP selection criteria take effect. Proposed FSWP changes should come into force in early 2013." http://www.cic.gc.ca/english/information/applications/skille...
List of non-LMO work permit options: http://www.cic.gc.ca/english/work/apply-who-permit.asp