I generally consider the more successful years under the Tribune to be 1984, 1989, 1998, 2003, 2004, 2007, 2008 (I know years like 1993, 1995 and 2001 fall into your swagging). 1993 was meh, 1995 was exciting when they won like 8 in a row at the end to get into playoff contention, 2001 felt great until the bottom dropped out in August/September.
Under Ricketts, sucked ass 2010-2014 then 2015-2017 were the best consecutive years of Cubs baseball that any of us will ever see in a lifetime. NLCS 3 years in a row and a World Series title.
For the Tribune years, it felt like the good years were spread out quite a bit and almost dumb luck while with Ricketts, they did the whole suck on purpose thing, brought in Theo and then we had that run and at the time, I thought the Cubs were positioned to be that good for a long time instead of fading back into a mediocre state of existence.
I don't think the current ownership gives that much of a horsefeathers now. The 2016 Cubs will be like the 1985 Bears in like 20-30 years, at least I am old enough to have seen both championships so I guess it isn't that bad eh? lol