Few things to be considered.
As a contract worker; you may have to manage your own accounts/ health insurance etc.
Have a good network of agencies/ friends circle/ network to help you landup into new contracts.
Ability to quickly pickup new skills and most important acquire new skills at your own cost.
Ready to relocate even for short assignments.
As contractor clients expectation will be very high; hope you are game for it; ready to put up long hours if reqd :(
Your total years of experience and in the insurance firm or wherever you have worked earlier; the kind of platform you worked or technology used makes an important criteria to land a job or fee you can expect to charge.
Apart from team size; other factors like volume of business transactions, software used, your location etc do count.
Contacts would be your current/ previous collegues, constant networking/ acquiring that new skills.
Finally you have to hook up with almost any agency which does help software testing related positions. browsing web for opporutunities including job sites, company sites etc.,
My best advice is that you should atleast have 4-6 months of back up money before you can start getting into contract position; evaluate if you can work short term assignments and best of all can you handle your own accounting