Yeah, I believe Jake is a legendary figure in the WWF/WWE. Like you said he has had some memorable feuds but just never held a top tier championship. His best feud IMO was with "Ravishing" Rick Rude, probably his most memorable too. His short feud with Hogan was cool, I can remember when he kept getting face chants, and the people were shouting "DDT!" when Hogan was a top face in the company at the time.
Who's Next- Hmm... Tully Blanchard.