Bob's last two or three seasons represent a very nostalgic period of the show for me... but looking back 15 years later, this seems like a pretty bland era. The Showcases in particular seemed to lack the excitement and spontaneity of the previous two decades. There was always three prizes, no more or less, and the skits were corny (or at least cornier than usual) and predictable.
For me it goes back a bit further than even that. I really started watching/recording the show regularly in Season 30 as a high school freshman, and I lived and breathed the show back then. I talked about it even in school often and became known for it, to the point that one teacher had a party for Bob's 80th birthday for me, complete with decorations and all and getting to watch his 80th bday daytime show in class that day, and getting a framed picture of Bob that all my teachers signed when I graduated in 05. So I was pretty much a lifer for the show and Bob at the time. Would been a dream of a lifetime for me to get on the show and meet him then, I'm sure some that knew me expected I might at one point even.
But when I look back at it now? Knowing what I know about how Bob was off camera, and just how the show overall was at that time as a result of that, I view it very differently. I actually tend to be more likely to watch older years of the show (particularly the Olson era, specifically in the late 70's/early 80's) than I am some of those just because of the different feel the show had, not to mention more time to actually let shows breath and let Bob talk vs. rushing through one segment to get to the next cause you basically had to.
That time will always hold some significance to me just cause it was a part of my teenage years, but....there is definitely some rose colored glasses around that to be sure. I still tend to like Drew a bit more as a host than Bob for that reason actually, because even if he's not as polished, I feel he cares more about the contestants and staff for that matter than Bob did, particularly in those final 6 years. Kinda brought back an atmosphere that was missing for a long time once he had settled into his own, and it needed it.