Ditching the phone company

Hi everyone this is my first post, I looked but really couldn't find a good guide to this so if it has been covered in another thread please point me to it.

The backlight on my Pre recently died so I am only able to barely makeout a few things on the phone although it still works for calls and such so I am switching back to my old dumb phone to ride out the last 4 months of my contract with sprint. After this contract is done it is my intention to completely ditch the traditional cell phone company relationship in favor of a VoIP solution that relies almost exclusively upon WiFi using either Line2 ($10/month or $50/6 month), Sipdroid/googleVoice (free after porting charge), or some other similar service and using either an iPod Touch, an iPhone, or an Android handset. As a backup for when I am not around a wifi connection I was planning to do a prepaid SIM card with either ATT ($.10/min) or T-Mobile ($100 for 1000 min that lasts 1 year). The other option would be a mobile hot spot ($40/month from virgin) but that is pretty expensive IMHO since I already have wifi at home and work and would require carrying and charging an extra device.

Has anyone else done this or something else similar? If so could you please share your experiences, tips, pitfalls, etc...

Like I said I have 4 months to plan this out so I have time to find a device and I don't have my heart set on an iPhone or Android so I could go with either.

After doing some research it is looking like either a Nexus S or jailbroken and unlocked iPhone 4 picked up cheap from an ATT deserter is my desired handset.

The dream is to be able to have a smart phone for internet access anywhere with wifi and a phone available anywhere for $200/yr or less.

If I went with the Nexus S what options do I have for a software/services stack to make this happen?

Must have requirements:
-Porting my existing number
-Ability to make and receive unlimited phone calls to US and toll free numbers over WiFi
-Ability to send and receive unlimited text messages over wifi

Nice to have but none of these would be deal breakers:
-Ability to automatically forward my calls to my SIM if I can't be reached via wifi
-Ability to transfer a call to my Prepaid SIM and continue seamlessly when I go out of wifi range
-Ability to automatically forward my text messages if they cannot be delivered via wifi
-Easy to use, I am highly technically knowledgeable but if it is easy enough to use I could convince my wife to drop the expensive real phone service
-Online backup systems, Palm's implementation is really slick example of how a smart phone can be totally independent of a computer and never ever NEED to be plugged in

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