It definitely will take a lot of work to scale it, but I think it can be done. I could probably be watching 3-4 cities at a time fairly easily. Portland has a very active Craigslist community and I have a lot of down time waiting for new ads to come up. On the other hand, if I'm always at the computer, I lose a good chunk of profit on items I have someone else pickup, so I have to increase volume to make up for it, which is not always easy. I'd love to hear your thoughts and suggestions, as this is my main hurdle I'm facing right now.
I'd say that a netbook with 3g internet would be a worthwhile investment, so you could check for new deals even while your out on the job. Then you'd always have your next destination, you could plan routes efficiently, etc.
I have a 7" samsung galaxy tab with built in 3g from verizon. I also have a dash mount so I use it as a gps as well as to pull up emails, addresses and listings on the fly. It also acts as a hot spot to give internet to my laptop when I'm traveling.
Couldn't you make some application which scrapes Craigslist every 5 minutes and detects newly posted items, maybe filter them on some criteria, and SMS them to your phone?
The CL app can do that for you. Say, you save a search for "refrigerator" in a certain area, in the "Free" category, the app would notify you (it puts a # on the top bar of your phone) letting you know there's a new listing for "refrigerator". Same thing for "roommate" or "carpenter" jobs, etc.
It's pretty cool, wish I've known this app when I was looking for a free carpet.
Interestingly enough, just last month, I bought on CL and sold a pair of girl's snowboard boots for $15 more in a matter of 4 days. Mostly because I really didn't want it.I was just practicing on my selling skills. I'm more inspired after reading this.
