Best practice for uncashed cheques?

[Marc Sherman]

How do folks handle cheques they wrote a while ago but which remain 
uncashed for a while?

Up until now I've been leaving them in the register with the original 
date written on the cheque, but I'm having increasing trouble figuring 
out where the missing money is when I go to reconcile with downloaded 
transactions from the bank and my current balance doesn't match my 
cleared balance.

I've been toying with the idea of moving the dates forward for these 
cheques to the next business day after I import/reconcile. That better 
reflects the current reality -- those cheques could be cashed any time 
in the future, so my current balance is correct and my future balance 
best predicts the worst case scenario. Also, the act of finding and 
advancing the cheques gives me a chance to chase down the person I wrote 
them to and, if needed, gently remind them to cash my cheque.

But it's a pain to do this -- is there any way to automate it?

- Marc