Losing the older dog was completely unexpected, but now that it is over the house sitting issue isn't quite as daunting. We had just chosen someone who was willing to take on the responsibility for him, but it was still a worry. I'll let you know how the whole experience goes.
I initially used two sites several months ago:
http://www.luxuryhousesitters.com and
http://www.housesittersamerica.com. I got WAY more responses from Luxury House Sitters, but a lot of them were either way too young (we're talking 19-20) or had other background-check issues. I got two appropriate candidates from House Sitters America and chose one. She ended up backing out (with plenty of notice), so I started over. This time I used Luxury House Sitters and and another site I found,
http://www.trustedhousesitters.com. EVERYONE who applied from the new site was well qualified, but I got another slew of unqualified people from LHS (I did get some good ones, too.) I think the difference is that there is a small ($10) fee to use the site even for homeowners, so it isn't full of flakes. Ultimately, it came down to a choice between a 20-something couple and a couple my age (late 50's). I sent out the agreement to both of them and the young couple passed (I intended to interview both of them.) So, after some back and forth with emails, I spoke to the remaining couple on the phone, felt we clicked, and gave them the job. The next day, the dog had a stroke and that was that. So, at this point, we're as confident as we can be that the people we chose will work out fine. I sure hope so because we're planning more ambitious travels for 2014 that won't be as easy to cancel at the last minute as a road trip.
Of course, I'll fill you in on what ultimately happens. It is a bit concerning because there really isn't anything to obligate a house sitter to actually show up other than being a responsible human being and fulfilling a promise to a complete stranger. On the other hand, even if we were to hire someone and pay them, that doesn't mean they won't take the money and run, so it is all a gamble. At this point, we're optimistic that it will work out fine.