Putting to one side the line/output/(expected)guitar signal level issues I really don;t think going to all this trouble is going to be worth it. As I said wearlier there are plenty of delays even with Cubase Artist - you can also download Steinberg’s vintage tape emulation delay free (Karlette) http://www.steinberg.net/en/support/unsupported_products/vst_classics_vol_2.html
If you’re new to all this then trying to confuse yourself with outboard effects is pointless - particularly as delays are one of the effects where, IMHO, the type you use doesn’t make that much of a difference - it’s how you use it that counts.