First I want to say it is good to see more resources directed to the game again after a (at least IMO) long period of decline. JOverseer might be a great tool compared to older Input Options, but why don’t take the consequent step towards a web-based order Input System? A page where Players could log in, input their orders with all the assistance JOverseer is offering ATM and finally where they could download their results. I am certain this could be done with limited technical effort AND would save a lot Manpower afterwards.
Still, there would be development costs. I already proposed some time ago to finance it with Kickstarter. That way you have a nice way to find out how large and how willing to invest your Player base is. I sure would donate some Money and know others who would. If you don’t meet your Goal - OK then bad luck and People get their Money back. Not much risk there.
With a new and shiny user-Interface, it would much more likely to attract new Players and get back old ones.
My two Cents