I would say yes to Jake, no to Boss Man. For me, I look at ring work, promos, length of career as a regular performer, titles, and their impact on the business, how often did they main event, did their biggest feuds draw money, what major shows did they main event or have a significant under card match that was highly anticipated and contributed significantly to that event's success.
Jake Roberts was one of The Top 5 guys in WWE from 86-92. He didnt main event a lot with Hogan and Savage on the roster but his feuds were often in the top 3 in importance at any given time. He was easily one of the most memorable villains of his time, his promos and the python attacking his opponents was priceless. Great feuds with Savage, Rick Rude (rare face turn) & Undertaker. He also did good work in early 90s WCW.
Boss Man to me was the quintessential mid card guy, popular enough that beating him was important but not big enough to be a legit main event championship contender. Did Boss Man ever main event a WM, SS, RR, Starrcade, Great Am Bash, or even a Sat Nite Main Event or Clash of Champions ? How often was his feud of the moment big enough to be among the top 2 or 3 bouts on 1 of those shows ? Savage didnt main event WM3 but his bout vs Steamboat was huge for that show, same with Dusty Rhodes vs Tully Blanchard at GAB 85. I just dont remember Boss Man being in that league very often. Finally, did he ever run extensively vs any of the Top Guys of his time like Hogan, Savage, Flair, Sting, Luger, Hart, Taker, etc and how big were those moments ?
Jake yes to HOF, Boss Man not so much