What’s the best way to go about finding places to live for a short time that don’t cost an arm, leg and rib?
VRBO & HomeAway have been pretty solid senders, we've tried a bunch of other options, but I don't think we've ever managed to book via any other site (except for one rental straight through the condo complex in an area not well-served by HomeAway/VRBO). Searching VRBO is a pain in the neck, but the owners tend to be a lot more experienced.
But there's a startup idea--someone should get on it if they haven't already--"Priceline for VRBO/HomeAway/AirBnB."
You absolutely have to haggle. Every time. Even if you're only staying two days, ask for a discount because you're a quiet computer programmer who knows how to clean up after themself. Other good reasons include last-minute offers and long stays. I've knocked 50% off of ~50 nights so far, the usual discount for even trying anything is 25%, and only once has none of the half-dozen places I've contacted not taken something off the price.