iTunes Match Alternative ... or some way of implementing this
I had some kind of similar question here.

I decided to go my own route, because basically everything from big companies is specific to their environment. And even though it required some work, I ended up with a solution I am quite happy with.

I have a Mac Server and a DynDNS service.
I have a Madsonic Instance running, which is a fork of Subsonic.

Subsonic has a lot of Apps that can be used for streaming.
Madsonic (and any other fork) is compatible to those clients.

Subsonic wants 1$ per month, if you want to use streaming (via Apps),
Madsonic (and most other forks) do not.

The Web-UI is awesome and there are also other Web-Clients like JamStash
,
that I love to use personally.

Besides the Subsonic Setup, I have a very cleaned up iTunes Library that has Home-Sharing enabled and can sync via Wifi with my iPhone. Also including my purchases.

iTunes requires a lot of attention and maintenance as I discovered recently;
and I would not recommend to let iTunes manage the Library itself.
Instead I wrote some scripts (and found some)
to make maintaining my Library a lot easier

I decided to build up a Folder Structure, that I like
and only let iTunes reference those files, but never touch them directly (except for metadata).

Subsonic does not care about the management, it simply searches for new media every day/week/month (as you wish) in a folder and updates the library.

However, all of that requires a lot of work.
If you are lazy or you simply do not care that mouch about Music, You should use another Service besides iTunes Match, as other Users also suggested (Amazon Cloud/Spotify/Ecoute/...)

From where we stand today, I am very sure, that there is no solution to a good music-streaming service that we seek.