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Seeking Advice – Want Better Phone, But I’m Mid-Contract (and Cheap)

I’d like to get a better smartphone.  I currently have a Blackberry Pearl with 2 yrs left on a Telus contract.  Anne has my previous phone which is some kind of Samsung flip phone with about 5 months left on a Rogers contract.  I’ve been to both places and have been told that to upgrade to a new phone I need to pay full price. For a decent phone that’s about $500-600 which is too much.

Here are the phones I would consider upgrading to.

• Blackberry Curve, Javelin or Bold
• Blackberry Storm (maybe)
• HTC Touch Pro (maybe)
• iPhone

Here are my options as I see them…

1. Pay full price for a phone at Rogers (probably iPhone or Javelin) and then be contract free in 5 months.  Sounds good but I don’t really want to spend the money.  Frankly, once my contract is up at Rogers I’d kind of like to not deal with them anymore.
2. Pay full price for a phone at Telus (probably Curve or HTC Pro) and keep my current contract/plan.  Again, probably too expensive.
3. Buy a used phone and activate for Telus or Rogers.  The person I spoke to at Telus today suggested Craigslist (Toronto) or kijiji.com as a good place to get phones for less money.  Looks like I could get a replacement phone for somewhere between $200 and $400 (or up to nearly full price really).  I worry though about the trustworthiness of those selling the phones and that a good deal might end up being too good to be true.
4. Be patient (not in my nature) and wait until Rogers contract is up, then get a new phone for the 3 yr contract price (about $200) at any cell provider.
5. Call Telus or Rogers and see if I can convince them to offer me a deal on a new phone (that for whatever reason the store clerks can’t offer).

What frustrates me about this situation is that to get an affordable phone you need to sign up for a three year contract, but the technology is moving fast enough that I don’t really want to use the same phone for 3 yrs.  It seems like there should be some accomodation by these providers to encourage upgrading even if it’s during the contract period.  Doing so would promote the use of their products and networks, and would also lead to customer loyalty.

So, as you can see, I need your help.  What should I do?

Updated Apr 27th: Rogers was able to offer me a phone at nearly the 3yr contract price ($249 instead of $199).  Since I was only a year into my contract any offer from Telus wasn’t going to compare.  So, I’ve ordered the iPhone and Anne gets my Pearl.

Updated May 3rd: I love my iPhone.

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