Fortunately the agency that I have been working with for my contracts has been very by-the-book when it comes to their pay practices. All of my contracts have been at a flat, hourly rate and have had all of the appropriate taxes taken out just as they would be in any standard W-2 type position. I've been approached by other agencies that promise the moon and the stars and assure me that they can put me into a local contract with all the tax-free goodies to boot! I actually have found it helpful, because it has reduced the list of potential agencies I want to utilize VERY rapidly. I am leaning towards the retirement advantage of a C corporation as my intended structure. I am fortunate to have exceptional health coverage through my wife's employer, so the advantage of subchapter S doesn't get me too excited. However, as my current salary is adequate to provide for the day to day expenses, the ability to exponentially increase my retirement savings has me swooning. Within that framework, though, is there a significant change in how I would "pay" myself from the corporation given the lack of tax free stipends? Or am I overcomplicating this? (perhaps a conversation better suited for an email exchange?)