After a bunch of reading and trying to decide, I dove in today. I had planned to downsample my entire library of lossless files into a separate library to use on our iphones, as we went with the 16 gb versions. I have a laptop/dacport and a 64 gb touch 4G/pico slim for lossless files when I want them portably. I would be using the phones for only on the go, with either Yuin PK3's or the dreaded ibuds (not that bad when you are working around the house, need to hear other things, and might need to answer the phone).
It turns out that match downsamples to (or replaces with) 256 kbs files. Good enough for the iphones. So far, it seems to work pretty well. @bhd812, I wouldn't be surprised if you are STILL uploading a bunch of your library. I started last night, and it is still uploading, and I only had a couple thousand that needed to upload.
There are a few odd glitches, but for the most part, it is working for what I intended it for. If you "need" lossless quality no matter what you are listening to, or where, well, skip match. If you can live with what I consider quite good to excellent lossy quality (I've experimented a bit, I think I can tell a difference up to 320 kbs. *think* I can...) for on the go listening, match is darned convenient. If you opted for the 16 gb storage on your iphone, it is brilliant.
If you are not an itunes user, well what are reading this for!