I am in the same boat as well. I love my HTC Imagio, and I am eligible for an upgrade. I want to get in before Verizon does away with the unlimited data for $29 plan.
I just purchased my first Android phone, for my daughter, a Samsung Continuum. It rooted in 30 seconds, no data loss, an I had it tethered wirelessly in less than 3 minutes. The phone is FAST, smooth, and feature filled. I fell in love when she played the HD Harry Potter trailer.
I am down to 3 choices for my phone(All three are easily rooted). (The links work)
Droid X (Price is good)
Samsung Continuum (My daughter has one and WOW.)
Droid X2 (DUAL CORE)
I am sold on Android after many years of WinMo.
BTW: I will be selling my HTC Imagio. Been in a silicone case since day one and never gone without a screen protector. Already unlocked with HSPL and I can leave the EnergyROM on it.