[GNC] Checks outstanding...VERY outstanding!

[Eric H. Bowen]

I have a few vendors and charities whom I still pay with paper checks 
(they're not eligible for my bank's electronic payment system), and some 
of them are very lackadaisical about cashing those checks. It's not 
unusual for one of them to sit on a check for three months before it 
finally shows up in my bank's payment queue...by which time it's long 
past even the maximum possible setting on GnuCash for manually matching 
a check. More annoying, and this has happened several times, is if I 
don't watch the match game with an eagle eye GnuCash will then assume 
that the paper check from a month and a half ago which just cleared is 
actually the one which is supposed to go out tomorrow and will mark *it* 
cleared...and then there's no way to "unclear" it in the matching 
algorithm. Oh, I can manually hit the check box and change the clearance 
from C to N, but the next time I download transactions it will skip over 
that one and not clear it, even when the proper check finally does come in.

One of the issues is that, according to my best understanding of U.S. 
tax law, payments are officially "made" when the check is written and 
dropped in the mail. So, if I write a check in November but it's not 
cashed until March (which has happened)...it screws everything up, and 
(even if the check is still within the window to manually match) "Update 
+ Clear" brings the payment out of the proper accounting period. So, 
does anyone have a recommendation for dealing with this kind of kerfuffle?