running KMyMoney 4.14.2 on Linux Mint 17.3 Cinnamon 64 bit
Is there a way to schedule a transaction that doesn't have an exact repetition, i.e. like Social Security on the 4 Wednesday of the month?
I've tried this using say the 28TH of the month, but then I have to go to each transaction and change the date. Also when I do this even though it's marked to automatically enter into register at due date it shows up 'greyed out'.

KMyMoney 4.14.2 does not exist. That is probably KDE 4.14.2. Please use Help/About KMyMoney to extract the version info not Help/About KDE.

Unfortunately, no matter what the KMyMoney version is, such a scheduling feature is currently not supported.

Scheduled transactions show up in grey. Once entered into the ledger (either automatically or manually) they will show up as a normal transaction. Depending on the number of days you display scheduled transactions in the advance (there's a setting for this timeframe) the next schedule might show up as well.