T-Mobile MDA with To Go and Wi-Fi?

A while ago I was looking at every phone and every plan. Eventually we found T-Mobile To Go, and it is the perfect plan for me, since I never talk on the phone. I've been paying something like $15 a month or less in total. So that part is great. I couldn't decide which phone to get though, and I was in a hurry, so I just got the cheap T209 that they had at Target. I am relatively happy with it. However, all along I have had plans for something better:

I want to keep T-Mobile To Go, since the phone part is a good plan for me.

I want to get a smartphone, though, as I am totally addicted to the internet. But I want to use my To Go SIM card in it.

What's the point of getting a smartphone if you are aren't paying for a data plan? Well, a number of phones have Wi-Fi, which would enable me to surf the web wherever there's an open access point, right?

That exposes me to security risks, though, so I would want to encrypt everything I do and send it to my home router, which would then unencrypt it and proxy it to the outside world. So everything I do online will look as if it's coming from my home IP, no matter where I am, and anyone trying to sniff the traffic going through their access point will just see a lot of encrypted data going to a single IP. I think this is feasible, but I'm not certain how. I have DD-WRT on my router, so I can use its built-in VPN feature for part of this?

Then I'd like my phone to support Skype. :-)

Is this a crazy idea? The T-Mobile MDA and SDA both have Wi-Fi, and apparently just barely support Skype (only with overclocking?) I only want to spend
 
WiFi on a cellphone is no where near the speed and quality of WiFi on a PC. keep in mind that the main drivers are the connection itself, the phone's processor, and available memory. The latter two not being strong points of handhelds.

As for SKYPE capability, I don't think the throughput is there to support a usable connect via a cellphone/WiFi connection. Its getting there, but just not yet.

I wouldn't be so concerned about encrypting your data via a public WiFi. Just be smart about what you are doing. As long as it is just surfing, then you shouild be OK. In any case, you should not be doing anything dealing with financial or other sensitive info over a public WiFi network.
 
I don't see how this matters. I'd like an Internet connection when I am not at my PC. A slow one is better than nothing.
This says it works.
Everything I do online is "sensitive". :-)
 
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