I think one of the problems with building software for freelancers is you are targeting both $5/hour Elance and $100/hour 'ninja' workers. In the case of Proper

I think one of the problems with building software for freelancers is you are targeting both $5/hour Elance and $100/hour 'ninja' workers. In the case of Proper (nice landing page btw!) both may have the same usage but will get a different value out of it - meaning you can't charge them both the same price. One way you could get around that in you product offerings is to offer more features in the higher plans than just more usage.