Another soul saved from the hells of repetition!
I don't know Quicken, but put generally the script should look like this:
The commands to use: WinWait, WinActivate, WinWaitActive, Send, Loop, Break, Goto.
Startup: Set up the program, load the files, go to the right place.
Looping: Use Loop to repeat the core actions. When you reach the end, there's got to be some detectable change, like a changing titlebar or statusbar, the data fileld is empty, or something, and then you use Break to quit the loop. Goto does the same thing.
Ending: Clean up.
There's no ends to what can be done with AutoHotkey.
I once transferred a customer's old DOS-based database to a new Windows based one by copying and pasting field by field, saving him (or me) weeks of work! It only people knew...