It should, but you'll need to partition it correctly and a file system that support it (SFS, PFS, OS3.9, etc.). Same as any setup on an Amiga with a large hard drive. 
Thought so. I have an A1200 but needs HD, floppy drive, maybe KS 3.1 since I have 3.0, and an Indivision. Dont know if I want an Indivision since I cant use a widescreen LCD.