First of all, FreePascal already offers 64-bits support. It's not Delphi, though.
Second of all, I expect about the same problems that existed in the time Delphi 1 was upgraded to Delphi 2. The biggest problem is is mostly address-space related and the problem here is that pointers will be widened from 4 bytes to 8 bytes. In WIN16 they use to be 2 bytes and a trick was needed to get over the 64KB boundary by using segments and offsets for pointers. (With the possibility to use default segments for several tasks.)
It's also likely that certain datatypes will become bigger than they are now. The integer-type will be 8 bytes, most likely. (Used to be just 2 bytes in Windows 2.) Enumerations will likely become bigger too. But most other datatypes are likely to keep their current size, so not too many changes here.
Another issue will be memory requirements. Since pointers will be 8 bytes long, an application that uses a lot of them will also eat up a lot more memory. A list with 10.000 pointers will increase from 40.000 bytes to 80.000 bytes. You might want to use a bit more memory than on a 32-bit system.
Speed will also change a bit. Since the processor now handles 8 bytes at the same time, it can process data much faster. But since pointers and some data types become bigger, receiving or sending these to some device or memory will be a bit slower. In general, your applications will be slightly faster in general, but some parts might actually become slower!
Finally, changes in the Windows API will require you to use the 64-bits API functions. Maybe the Delphi compiler will do something smart to allow code to call 32-bit API functions, but this would slow down performance because the processor now switches between native 64-bits mode and emulated 32-bits mode.
