I'm working with an post exit software entrepreneur(who's backing financially) to try to figure out a way to get transportation solution for the poor. Rather than just giving them a car, we're considering a free or significantly discounted zipcar like service. However to figure out feasibility we need to figure out what type of costs are involved.
Anyone on HN have any ideas on how something like this could be insured/infrastructure set up, or pitfalls to look out for?
We've got some donated cars, which have been fixed and "guaranteed" by the local Toyota dealership for free (great people). Now we just have to figure out the best possible way to expand such a program
Something to look into is how many people will have a smartphone. If not many (or for the ones who don't) I'd give them a cheap Android phone that does nothing but run your app. The phones can run on a group data plan (and like Republic Wireless' phones, WiFi whenever possible), and just be a more powerful kind of key fob that lets your members find, request, schedule, etc. cars. You could also use it as a key, requiring a password in the app to send a bluetooth signal that unlocks the car. I might also use these phones to connect to the cars' onboard computers whenever the car's in use, so that you can check fuel levels, engine status, etc. Some of that may be a bit further down the road -- you may want to go with more lowtech solutions while you get this up an running.
re: insurance and infrastructure, the best thing you can do is talk to people at ZipCar. You're not a threat to them, and they have the exact expertise you need.