I think it's a shame airlines are not required to rebook and would rather see passengers stranded.

If Soutwest does not have the technology to rebook on other air can they not simply issue some kind of voucher like when airlines issued food vouchers? Or let the passenger do it rebook themselves and submit the bill electronically.

Air travel is a very complete operation and flights will get cancelled. It's about service recovery.

In Canada airlobes by law must rebook on other cariers when a flight is cancelled. The waiting period depends on the reason for the delay. Front line agents have gotten used to the extra work; instead of seeing a family stranded for a days they simply issue a FIM manifest and get them on their way home. The passengers are happy, the airline benefits by filling a seat on a competitor that might not have been therefore allowing the next available seats for sale on their planes open for sale.