So far, I have not had to purchase any software. I also haven't had something I used to use that I really can't now except my Windows development tools, which was to be expected.
For software development, I had a collection of Delphi, C++ Builder, JBuilder, Compaq Visual Fortran and Matlab. I no longer really use Delphi and didn't use JBuilder really since I'm still learning Java. The Mac has Java development that I can pick up on since I'm not invested in PC Java. The Mac also has C++ development included. For me, I don't reallly have PC apps in Delphi or C++ that I need to port over (although I may try as an exercise) since my home programming tends to be recreational. The Fortran and Matlab are for work, so they are not my investments. I never really use the Fortran at home. I do more Matlab at home, and fortunately, there is a Mac version that works very well that I have installed. I recently found and installed a Mac Finder extension for the Subversion version control software that I use that gives a very similar GUI interface to it that I have for Windows.
For everything else, I was not very invested in Windows software at all. This probably had a lot to do with all the open source software I made use of. I also didn't have a great need for "office" type apps at home - the most typing I do aside from programming is e-mail. For the occasional Word or Excel attachment I get, AppleWorks seems to do fine. If I really needed MS Office compatibility, there's always the Mac version. Also, much of the hardware I had didn't even need drivers installed. Granted, I tried to buy hardware recently that was Mac friendly where I could. My Microsoft scroll wheel mice, Thrustmaster joystick, APC UPS, Canon digital camera, Canon DV camera, Canon Printer, and SanDisk CompactFlash reader all worked when plugged in. The Sandisk reader isn't even listed as supported, but showed up as a picture source in iPhoto represented by a icon that looks just like the reader. Also a USB to MIDI adapter just worked, whereas Windows XP had to have a driver installed (but that's what you get with an OS that hasn't been really updated in 3 years).
I've talked about my Palm PDA previously, and I may end up purchasing the Missing Sync, if I feel the few extra features it brings are needed. I did recently get the Mac version of Plucker (another free tool), which I used on the PC to download websites and newsfeeds onto my PDA. There was also a Mac version of the time synchronizer, so my Palm's clock stays in sync with my Mac, which is synchronized via the built-in function with time.apple.com.
Games is the other weak area on a Mac, but I'm not much of a gamer. I've got several PC games lying around I bought in the last few years, but didn't even have much time to play them on my PC. I was more into them when I was younger and single. I was an early adopter of network gaming, but we did DOOM and it's derivatives, with a favorite being Heretic. I recent;y found the Mac version of Doom Legacy and can play those classics on my Mac mostly. Unfortunately, the Mac version still can't play networked.
For Internet stuff, I was using Mozilla and Outlook Express on the PC. I now use Mac Mail, Safari and Mozilla on the Mac. I use Mozilla now only for newsgroups. There's IE for the Mac for the odd page that Safari doesn't deal with. For chat, there's iChat for AOL IM and Yahoo! Messenger, although the later does not have audio in the Mac version, but it does support my DV camera for video chat. I can also use VPN to connect to the company's LAN from home (or even the sofa at Satellite Coffee) - something I've yet to get to work on my Windows 98 box. Mac AddressBook replaces Windows Address Book, and the photos of friends I put in there automatically show up on e-mails from them in Mac Mail.
For photos, iPhoto does a nice job. It has some weak areas, but it's already leagues ahead of anything on the PC in terms of ease of use. I got Adobe Photoshop Album for my parents on their PC as about the simplest photo organizer I could find, but it still confuses them sometimes. Adobe don't make a Mac version because it would be ignored in favor of iPhoto. They do sell the nice Photoshop Elements for the Mac, which can work with iPhoto to allow more sophisticated editing. A likely purchase for me soon, but I haven't tried the GIMP for Mac yet.
For music, it's iTunes of course. I had been using it on the PC for a while already ever since it came out for Windows, and have turned several people at work on to it. Some use the sharing feature, which creates an extra social interaction. For other media players, I have the free Mac versions of Real Player and Windows Media Player. There was even a Mac version of DivX, so I can play those as well.
I also found Xephem, some free Unix astronomy software that works on the Mac under Apple's X11 server. If I want something fancier, I can buy one of the versions of Space.com's StarryNight software.
Some other stuff becomes obsolete, or nearly so, like GhostView/GhostScript for viewing PostScript files. The OS X Preview app reads PostScript (although it converts it on the fly to PDF first). Acrobat Reader, even though it is available for the Mac, is not really needed since Preview is so fast at PDF viewing.
There is stuff my wife uses that I may have a harder time replacing on the Mac once I get her one. She has a few of the greeting card programs and some cross-stitch software. These things exist for the Mac, but not very many of them. I'll look into that later.
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