I have quite a few box sets, and I wished to see them all under a single Album icon/image, with Disc 1, 2, etc. I tried a few approaches and spoke with Apple support too. My conclusion is that iTunes as a product/program has gotten so big, and is used so pervasively, and in such complex combinations (especially if you are a Match subscriber), that it almost has an organic set of actions, rather than robotic. I know that sounds odd, but Apple nearly admitted to such, suggesting in one of my issues, we just "wait it out..."
Regarding the multilpe CD issue, first I found it helpful while loading CDs to be signed out of iTunes. This in essence turns off Genius and Match, and allows you to deal solely with iTunes (local) and the CDs you are loading. Next, note how iTunes reads the meta/data file for the disk. It is at the mercy of the CD mfg, and there is not always consistency in the title text. For example, I had part of a 8-CD box say "Dvorak:" another part say "Dvorak - " and another part with either the colon or dash. After loading, I went into Get Info, and standardized on the use of the dash - and verified the order, disk 1 of 8, 2 of 8, etc. and then all the CDs loaded under a single Album heading as I understand you are looking to do. Other CDs had an embedded [Disk 1], and [Disk 2] in the title. You must remove these from the title, in order for iTunes to file them together and then make use of the "x of y" fields.
After loading, you can sign into iTunes and do Genius - then Load Album Artwork, and then Match. It doesnot make complete sense to me, but doing it this way gave me the results I wanted, which seem to be the same as the results you are looking for. Also, if the initial load have been messed up by iTunes/Match etc, you may need to delete the album and redo, playing attention to the steps described above. Good luck.