IMO, It's worth buying one (or more) iPod Touch simply to use as a dedicated controller for your music collection. The iPod touch is cheaper than most phones out there, including the Android models, not to mention it's not clunky either, (like all Android phones).

There are no fewer than 3 applications designed specifically to control Squeezeboxes for the iPhone/iPod platform. All are third party and the best is probably iPeng.

Sonos also has an iPhone app which might make more sense than buying its dedicated controller if you're on that platform.

The Sonos players don't have displays. They also use a proprietary wireless network, not your existing WiFi setup. This is good for people who don't already have a wireless router. But I think the premium you're paying for the system is very high. Their UI on their controller and PC-based programs is decent, but not as good (visual navigation and control) as the default web UI for Squeezebox Server nor iPeng.

The other products, Sooloos and Olive, really push their dedicated servers. Nice-looking enclosures, but apart from the auto-ripping of CDs on the Olive boxes, nothing you can't get with any PC, Mac or NAS running Squeezebox Server (even one in a rack mount case with a nice RAID setup). I wouldn't recommend putting a server in your listening environment (Olive-style) anyway.

There's much less tweaking (than there used to be) and definitely no requirement to install modules or plugins with the Squeezebox platform. This situation is getting better all the time, but it's already at the stage where you can install, scan your collection and simply start playing your music without much fuss.

The most technical aspect with regards to managing your own local music library is making sure that your track tags are all set properly and as completely as possible. This affects every streaming platform out there though. Bad tags means bad music organization and navigation experience. Squeezebox does allow you to navigate a folder structure however if you need to get around this or quickly play back music which hasn't actually been indexed into its database yet.

I've got over 37k tracks indexed right now and the whole thing is as responsive and navigable as if I had 10 or 20. There's no degradation in performance nor usage even with a decent sized library.

As far as online radio play, you can tune directly to URLs, save them as favorites (which I think is a little weak in current software versions) or go through the built-in index of stations (which is very robust). You can also go through what they now call MySqueezebox.com (formerly SqueezeNetwork) which is their free online portal/service which allows you to listen/connect without running any type of local server yourself. Primarily for online/radio-type music content, not your own music of course. Though apparently there's also a service where you can upload your own tracks I believe. The Squeezebox platform has arguably the best support for online radio play.

If you want to test out the Web UI for the Squeezebox platform, simply install SqueezeBox server and then install SqueezeSlave - on a different or even the same computer. Squeezeslave can run as a daemon and acts as if it's a Squeezebox player. Doing this you can essentially turn any "server" into a player as well if you wanted to mimic the Olive server platform.

You can then control any virtual player through the web UI and the audio will play on the computer which has it (Squeezeslave) installed. I use this to play back audio on my MacBook which acts as my third (and mobile) Squeezebox. The server software is installed on my PVR system in the basement and music is pulled from a ReadyNAS Pro. I could install the server software directly on the NAS, but since the PVR is on 24/7 I didn't bother.

You can also test out the iPhone programs by controlling this virtual Squeezebox, however note that those programs are all commercial and there aren't any trial versions that I'm aware of.