Do it! We just returned from a trip where we house sat for 6 weeks in an awesome location just outside Sydney and another 6 weeks just outside Melbourne Australia. It was very different than staying at a hotel or other trips we've taken because we were able to live with the 'locals' (which I'm sure you can do with a vrbo type of thing as well). I don't think you need to go across the world like we did (it was a way for us to try out ER for 5 months under budget), but some things you might find useful when picking your spot....
1) Weather - we wanted to get away from the cold so only picked locations that were, on average, 70 degrees or warmer!
2) Easy access to Activities / sights - or whatever your objectives are for your trip. For us, we wanted to travel and experience the world. We are not city type of people and prefer nature, so both our house sits were about 45 minutes from the city. We lived in a 4 bedroom water view home in Sydney's Central Coast, where they had about 20 beautiful beaches within a 25 minute drive (yes, house and car were free because we were house sitting). There were hiking and biking trails, quaint small towns, and even a local sailing club where we took a 6 week sailing course and joined as crew at the weekly sailboat races (that of course ended up with a few beers with the locals). A day trip to the city was also easy with public transportation....better than driving, especially when enjoying Australian wine at a festival!
3) Budget - is this a vacation budget or a traveling lifestyle you want to have? We wanted this to be a trial before we RE so we wanted to see if we can travel under the same monthly budget we have when we are at home. We were able to travel for 5 months and stay under our monthly budget despite big expenses on a month long scuba diving trip in the Philippines, sailing lessons and certification, buying two bicycles, renting a Campervan for 3 weeks to explore other parts of Australia, going on a week long tour to Australia's Red Center, flights across Australia (it's a big country!) as well as to / from the Philippines with a stop in Singapore, all food, hotels, car rental, etc. We did well and now scheduled,to leave again in November!
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