So, I've been looking at Classic WB. That page totally confuses me. Do you have to download and install with WinUAE on a drive? All of the versions listed are for different target machines. I am sorry to ask so many questions, I try to read up all I can.
Yes, you'll need to use WinUAE because the site is "legal" and the downloads are missing certain files contained on the Workbench disks.
I've installed several versions of ClassicWB onto HDF files and real hard drives using WinUAE (Amiga Forever version).
Just follow the instructions step-by-step and you can't go wrong.
The only issue I see is that you have a SCSI hard drive, so trying to get the data moved from your PC onto the drive is going to be a major pain. You might want to wait, order a 3.1 Kickstart ROM and find a SCSI-IDE or SCSI to USB adapter and that way you can install one of the more "pretty" versions of ClassicWB directly onto the SCSI drive while it is attached to the PC (WinUAE can mount it as a real Amiga drive). You can then insert it into the A2000 and it should boot.
Also, while it is still attached to the PC, you could download KillerGorilla's WHDload game packs from his website and install a few of your favourite games onto the hard drive. Come to think of it, you might want to track down a larger hard drive too.