Hi,
1. Yes, 32bit perl can run on a 64 bit Windows OS. It will run under WOW64 which means it is loading only 32bit versions of system libraries. It also means that it may result in redirected registry calls (redirected to WOW64 based branches). You can google/bing there impact of running any 32 bit app on a 64bit Windows for these types of issues.
2. If you run 32bit on 64bit OS then it will need to load the 32bit versions of modules and extensions. WOW64 in Windows can not mix 32 bit and 64 bit binaries in the same process space. This is important to know, especially if you are planning on running a 32bit perl as a CGI process under 64 bit IIS.