There’s a significant difference between the long and short term rental rates, and you’ll be paying the significant part, unfortunately. If you don’t mind a apartment or sublet room, I’ve seen rates down to $80-90/night, which is considerable cheaper than resort rates.

You need a Federal work permit to accept *any* employment in the US. As you may have guessed, there are those that flout the law. However, given the current downturn in the Maui visitor industry, if you lack the proper documents, you’d have your work cut out finding someone to overlook it. Off hand, I’d say your best bet for legal employment at short notice is in entertainment (musician, etc), if you can find an establishment to vouch for you.

I’ve attached a few links that should give you a good start.