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Is there a free way to wirelessly stream content to an iPod Touch (if it helps, 4th gen with latest 4.3.5 installed) without jailbreaking? If not, will iOS 5 enable me to do this?

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Can you clarify a bit more please. Do you want to be able to stream music from your iPod touch wirelessly? – Slick Sep 15 '11 at 19:54
I want to stream music /from/ iTunes on my Macbook /to/ an iPod Touch. – zpletan Sep 15 '11 at 20:38
Would Home Sharing enable me to do what I want (it's OK if the iPod streams from iTunes instead of iTunes streaming to the iPod). – zpletan Sep 21 '11 at 20:55

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Isn't this exactly what Home Sharing does? On your iPod, go to Settings > Music and enter your Apple ID and password under Home Sharing. Launch iTunes on your Mac or PC (and enable Home Sharing there too). Back on your iPod, go to Music and tap the More button, and you'll see an entry for Home Sharing. Tap that and you can play any of the music stored on your Mac/PC on your iPod.

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I couldn't figure out how to get the iPod to see my library. This did the trick. Thanks! – zpletan Sep 23 '11 at 16:47
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There are a lot of options for this. The easiest ones use a native iPhone application that will cost you a small amount (usually around $2.99 on the app store). But you asked for a free solution so I'll start with that:

Free Option

Jackson Chung over at Makeuseof.com has written a detailed explanation of how to stream your iTunes music library to your iPhone/iPod/iPad for free. It wont be the greatest experience so I'm going to include a couple of the paid options below as well.

Paid Options

These two options use a iOS application to enable the streaming:

StreamToMe — $2.99 on the App Store

Use StreamToMe on your iPhone, iPod Touch or iPad to play video, music and photo files streamed over WiFi or 3G from your Mac or Windows PC. No prior conversion or syncing required (huge number of formats supported without conversion) just tap the file and it plays.

AirPhones — $2.99 on the App Store

AirPhones sends the audio from your computer to your iPhone or iPad with virtually No Latency. Perfect for wireless, synched audio.

Finally, this option does not require an application installed on your machine as it runs a small server that is accessible via an iOS-friendly web interface on your device.

Remote Buddy — €19.99 on their website

The most powerful remote control solution for the Mac®. Control more than 100 applications, virtual keyboard and mouse, presentations, media center software and important system settings right from your iPhone™, iPod® Touch, your Apple® Remote or one of the many other remote controls supported by Remote Buddy!

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I hadn't thought of this. Absent an AirPlay solution that I can use from iTunes, this will work. Thanks! – zpletan Sep 21 '11 at 2:51
@zpletan I'm afraid a solution similar to the ones above will be the closest you get without jailbreaking. Apple has marked the APIs required to achieve what you want "private". This means only Apple can use them AND get into the App Store. If you're interested in Jailbreaking there are a few more options. – Samuel Mikel Bowles Sep 21 '11 at 3:37
That makes sense. Still, I want to make sure. (And no, I'm not interested in jailbreaking.) If nothing else happens in the bounty period, I'll award it here. Thanks. – zpletan Sep 21 '11 at 11:34
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I've used StreamToMe and can confirm that it works nicely and does what you want. – Adam Rice Sep 23 '11 at 14:08

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