Check Splitting-Why so difficult?

We had dinner in Chicago this weekend. Eight people. We asked, before ordering, if we could split into 4 checks. Everyone on the same bill sat next to each other. There were no split appetizers or sides between the groups. The waitress said they don't usually allow it, but did. When the checks came out, all hell broke loose. Apps were on wrong bills, glasses of wine were on the wrong bills. Things got heated, she blamed it on the check splitting. The total bill was over $1,200, so each bill was in the $200-300 range. With so many people using debit and credit cards these days instead of cash, it's hard to go out in a group and not split. Why do some places seem to have no problem with it, and others do. Is it the system they are using? I have great respect for the service industry and someone really has to have bad attitude for me not to tip well (and we tipped well, regardless). So I'm not slamming wait staff, I just want to understand.


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