Is it illegal for a bank to hold charges until you buy something dumb then run them trough to cause over draft?

It is your responsibility to balance your bank account and make sure that you have funds in there for any cheques your wrote or automatic withdrawls, not the banks.

I could write you a cheque today and you could sit on it for 6 months and I am still obliged to ensure the money is in there.

Some bills paid on line are paid via a mailed check. It will take time to clear. You need to do a better job of keeping track of what you have sent out. That is what the check register is for. There are also a number of computer programs you can use for this as well.

No, but your right it is despicable. I have had that happen where I put money in to cover a check. They process the bill that same day, but then they don't process the check that covered the bill the same day so that I incurred a INSF charge.