I had a good experience with Insteon. Plus I tied their SDK into a speech recognition system, so I can tell the room to adjust lighting as I want.
In addition to the SDK they had a web server - which took HTTP triggered commands quite nicely, to device or class of devices.

I found their SDK was sufficient to let me do the basics that I wanted - though their documentation was a pain to work with.

Very nice project. And not very expensive (at least for one room - you needed X10/Insteon devices everywhere you wanted it).

Insteon was nicer because it did dual transmissions - wireless and powerline - so I didn't have to worry about the house's wiring.

I'm going through the Rogers hassle now - I loathe dealing with them, but with the iPhone, they're the only game in town. I tried your calculator - very interesting, it really nails down the intense confusion the carriers play on to determine costs.

I run Vnet's iSip - a sip soft phone on the iPhone, which turns my iPhone into an extension on my PBX. Unfortunately, you need to jailbreak the iPhone if you're planning to use it to answer calls (I used to do this pre 3.0, now I just ring multiple devices, including the iPhone and hope for the best).

My5 with the PBX (with PBX-forwarding to my mobile number) and backdoor outbound dialing mean that my phone bills for outgoing calls is much lower than it otherwise should be (I'm still hovering around the $130/month mark including data, and feeling very ripped off).

The questionnaire process is very long, as you warned... and I'm sure results may vary. It was enlightening to see the results - but without data and without phone-specifics (e.g., iPhone only runs on Rogers), it limits the utility to me. That said, I'm sending all my fellow Canucks to your site. It may let them have a fighting chance, at the very least.

My spidey-sense is tingling...

I haven't seen nano mentioned anywhere. Two thumbs up for nano! Of course, on Windows, I use Notepad++, mostly because EditPlus is proprietary.