No Problem her with fpcupdeluxe. Win32 fpc/laz. you have to use the fpcupdeluxe for win32. I use fpc fixes32 and lazarus fixes20 for a production system.
I have told fpcupdeluxe to make a crosscompiler to linux/arm. Working since 2 years like a charm.
With other software, i compile on windows, transfer this to the raspi and can direct run on the raspi. Debugging is not direct possible in my configuration. With a other setup i am able to debug on the raspi with Lazarus on Windows. Working but not fast. Remote GDB can be boring :-)
BUT you have to deal with libraries from RasPi at Compiletime for some Components. If yot have linker errors, you have to look for the correct libs and tranfer these to windows an configure the right path in the project options. But this ist standard if you want to crosscompile.