Not cheap, but one option is an ICOM PCR-1000 plus the program TalkPCR. There's a more modest version called the PCR-100, but I don't know if there's a timer-capable program for it.

There's another radio in this league called the WinRadio. I gather it has some active development as well, so you might find what you are looking for there
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Jim


'Tis the exceptional fellow who lies awake at night thinking of his successes.