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The releases are, in this order (and that's also the order in which they should be installed):
More combo packs (PC only):
And others. There is even an all-in-one combo, presumably including the extra Deluxe content.
This concludes the old Sims: Maxis is moving on to The Sims 2, which has a fully 3D environment, better AI and higher hardware requirements, and is probably much harder to input fan content into, so I'm confident The Sims will remain as popular as it is now.
Unless stated otherwise, all releases are available for both Mac and PC. I've also seen "The Sims for Linux" announced on Simsbox.com (see the Sim links) but that was the Sims for PC running on WineX in Mandrake (or Mandriva, as it's now called).
The reason that the packs should always be installed in the right order is that each pack contains not only new files, but also updates of existing files. The most obvious file to be replaced is the only executable, "Sims.exe", which is an interpreter for the code in the IFF files - if the interpreter is too old, the IFF can't be read - but IFF files themselves may also be replaced to correct bugs. The CD needed in the drive to play the Sims will always be that of the highest expansion pack installed.
As this list implies, someone who installs Deluxe and then buys earlier (though in terms of additions, later) expansion packs, will have to re-install Deluxe again after these expansion packs are installed. This is because Deluxe is not merely a combination of the first two releases, but one big update compatible with all releases that came before Unleashed. (Ironically, it's not that compatible with Livin' Large; see Between Deluxe and Livin' Large.) Though released much later, the other PC combo packs probably share a place with Deluxe in the installation order.
Judging from a booklet that came with one of the expansion packs, Maxis hopes everyone who owned the Sims or Livin' Large will replace it with Deluxe or Double Deluxe. (For people who already bought the original packs, The Sims Double Deluxe promises to be twice the ripoff that The Sims Deluxe was, but this time the DD-exclusive objects are on download from the Maxis site as well. I can see why DD was released, though: it updates all pre-Hot Date objects and skins to the Hot Date categories and buyables system, thereby eliminating the pre-HD skin-naming and set-making rules completely. Unless of course stubborn fans keep using the old LL/HP packs - which is very likely.)
I don't have much experience with Makin' Magic or Superstar, but I've heard rumours of menu bugs, more in-game anti-nudity censoring and installation of corrupt soundfiles in Superstar. I don't know whether the latter has been resolved in MM; apparently the bad music files are extra piracy protection (the good ones are played off CD). The censoring can be undone by editing "PersonGlobals.iff", see Beyond the Gay Marriage Hack.
The "buyable skins" issue: Hot Date has two big changes, one in relationships (there are now long-term and short-term relationship bars) and one in the organization of the four categories Undies/Swimwear (these are the same), Pyjamas, Nude and Formal. Originally, the skins, meshes and CMX files for all these dress styles were inside the standard Sims FAR files, with the same mesh being used for the skinny male and female nude/swimsuit bodies. Then, at some time, the B300-bodies Swimsuit Pack was released which contained the same nude/swimsuit meshes with different names, mainly so that the defaults could be altered for one gender without altering the other. This skin pack has all but disappeared (a shame, as a number of skins were made with it, including the Rei Ayanami plugsuit skins) and, I again presume, been replaced with the Hot Date system. In Hot Date, the Swimsuit, Pyjama and Formal styles (but not nude, as that's not something you can buy) have become "buyable" and can be acquired "Downtown". On disk, they are now in a separate directory "ExpansionPack3/SkinsBuy" (moved to "ExpansionShared/SkinsBuy" in Vacation and later releases), not in one big FAR file but as separate, unarchived files, I assume because playing mix'n'match with CMX and archived mesh files can crash the game (personal experience) if the meshes are not in extracted form. Here are found skins and meshes starting with F (formal), L (lingerie, formerly "Pajama"), S (swimsuits/undies; it's still the same, although "lingerie" spells "fancy underwear" to me!) and, if Vacation is installed, W for winter wear. Superstar adds H (high fashion).
As these files can now be "bought", gone are the day of making clothing sets for Sims through manual editing and file-naming tricks, unless of course one has Deluxe but not Hot Date, in which case it gets a bit more complicated. Why? Well, the user IFF files contain both types of bodystrings, but the old set-making tricks don't work any more, so to change the defaults and remain backward-compatible with the original Livin' Large, one has to change both the old and the new bodystrings. How to do this is explained in Simple character editing. To summarize: the extra dress styles, and especially the swimsuits, have gone from names like "fmskn_" and "nuskn_" via "B300MaSkn_" to "F100MaSkn_" and "S100MaSkn_". Unlike the early standard normal-style Sims mesh types, which started at 001, the buyable mesh types start at 100, and hopefully all the B300 skins out there are now automatically assigned a S100 mesh by default.
Does this sound terribly complicated? It is. As complicated as the Sims skin- and mesh-naming system which, when I try to use it for a certain effect, sometimes unexpectedly works and sometimes inexplicably doesn't. The essence is: old ways to make Sims clothing sets may not work any more after installing Hot Date, and manual editing may be necessary.
A warning for people who are installing Hot Date, Vacation or Superstar (all three of which which generate new Sims for non-residential lots) and who have plenty of fan-made skin files: temporarily rename the folder GameData/Skins and replace it with an empty dummy GameData/Skins so the game doesn't use fan skins for these Sims (unless of course you want the fan skins to be used). Apart from the horror of finding that, say, a Sailor Moon Sim has an evil twin on Vacation island, mesh numbers that fan artists gave to their meshes have later been used by Maxis (since there isn't a real central index of what numbers have been used or are "reserved"), so there is an infinitesimal chance that two different meshes with the same number exist in the directory, and that the game, in creating new Sims, will produce some awful mesh/skin mismatches.
Lastly, it is common knowledge that six of the Hot Date buyable skin files contain errors. They can be found and corrected with fan-made CMX validation tools like the SimEnhancer freebie. There are also a number of spelling mistakes in the buyable skin names, most notably "L100FCChddrk_orignal.bmp" instead of "L100FCChddrk_original.bmp", as I found out when trying to assign a skin to a mesh directly; they don't generally hinder gameplay. These are mistakes that have snuck in in Hot Date and haven't been corrected in subsequent versions, so installing a new expansion pack typically means the skin file errors have to be re-corrected.
On the SSP pages that follow, I'll be referring to the expansion packs
as Deluxe, House Party etc. without italics, or with their abbreviations:
LL, HP, HD, UL (Unleashed). It saves a lot of typing, and from the context
it should be clear what version is being referred to.