to hear music you have 3 options.
1. aux output- cable with 2 male. control music from phone.
2. usb - control music from radio, but phone is on usb mode. so... will sit like a brick next to you.
3. bluetooth- can control from phone or radio. probably will pick up calls.

music cloud... Google Music app. transfer from itunes to google music and your good to go.
there are apps that will link your itunes music with another app and listen to them in android; but for this just do a little search.
and to root, if changes or new things makes you overwhelm, don't root. you are gonna freak out and take your rooted phone to sprint and void your warranty.

Go buy a Droid Bionic, Droid Razr or one of them new Samsung's. Most Smart phones have weak ass processors. Need to buy the cream of the fuckin crop for good performance. Ice Cream Sandwich update comes out in like a month or two. <Update will help

My Evo will still hang with the new devices. Root FTW

Evo is 2 years old and still fights in the ring with the big boys and holds its own. The only thing that could make it better is a dual core, the Evo 3D got a dual core but doesnt keep up with the original in several aspects.

As far as anything Motorola or Samsung,

Motorola is a major PITA to root, very nice and mostly easy once its rooted but really difficult to get it there.

Samsung SUCKS! Pain to root, and a major headache once it is rooted, shitty ROMs, major bugs, NOTHING ever works.

I used to actually root phones and install ROMs and things as a side project/job and it got to a point where I absolutely refused to touch any more Samsungs, and actually told the people that I had already worked on to sell the phone and get something else.

Android w/o Root is like Sex with your clothes on, access to nothing and you end up with a useless load in your pants.

l8r,
PD

Get the Galaxy Nexus. Yes it's Samsung BUT it's the official Google Developer device. That means it can be broke completely to the point where you can't even boot it and still recover it. Nexus devices are a must for any true Android nerd. Their extreme mod-ability is what makes them shine. I had a OG Droid and its community was great. Got the Bionic, complete crap. Now that Moto locked their devices down, the fun died off. Got the Nexus and I can consider it a TRUE successor to my OG Droid. It's really a great device and ALL updates come from Google, so no waiting on Samsung (which is terrible at getting updates out in a timely manner) to get a update out. Got the phone with 4.0.1, got the update to 4.0.2 about 20mins after getting it, 4.0.3 is coming in a few weeks as announced by Google.
Oh, and GPS works good. Something that most Samsung phones are bad at.

I have a photon. Really pleased with it, but if I go root, I'll be adding a couple of things which keeps me thinking if it will be worth the time. I know I can do 1k things but I want like 3 or 4.

i use one click to root my samsung epic, cyano7 is almost done on it. we dont have roms like the evo though. besides that its not that hard.

which epic do you have? the original epic 4g is a major pita lol, Ive been constantly working on a dozen or so. I hear the new Epic is better.

The Nexus S is a bad ass phone but lacks 4g, and in the ring with the Evo 4g it got its ass kicked in every battle except 1 which was the super amuled screen. Which I would absolutely love to have.

l8r,
PD