Re: Broken widgets work fine on chumby.com
You can't really strip the https from the URL and expect it to work - you need something to fetch the resource using https using the appropriate protocols and certificates, then provide the data in a form that the chumby can accept - this is what chumby's proxy server does, although it also provides a certain amount of caching.
The chumby itself has a small server, and I've seen some folks hack that to do something on behalf of widgets that aren't capable of doing whatever it is on their own - however, anything trying to do SSL from there would have the same problem as the rest of the chumby since it would be using the same protocols and certs that the Flash Player is using, since that's what's on the device.
It would be possible to set up another server that does stuff similar to what the chumby system does for use by third parties - however it would have to be crafted carefully in order to better handle busted or slow servers than the chumby proxy currently does. The chumby system was designed specifically and exclusively for use by chumby's internal developers who would understand and work within the rules imposed by that service.
As to whether I could do this under chumby's umbrella is really a cost question - I don't think, even with the subscription income, that I could cover the costs of proxying all of the data traffic to all of the widgets using https on all of the chumbys.