While I agree we have stronger foundations than in those years, this sentiment is littered with hindsight. I remember a lot of fans and pundits alike tipping us to take the next step in 09/10. Ronaldo had departed United, and for us Glen Johnson was seen as a missing piece of the jigsaw to provide attacking thrust from full-back. And while you'd have had to be a bit of a loon to tip us to win the league without Suarez in 14/15, especially with the quality signings Chelsea made that summer, there were plenty predicting we'd qualify for the CL again.
I agree with this in some ways. People were not predicting we'd be seeing a season of significant down turn at the start of 09/10. However, I think there is some mitigating circumstances in that situation. I don't think a lot of people realised how bad the off the field problems were. We were in a mess but not everyone knew that at the time.
Not hindsight but at that point a good proportion of the supporter base wanted Rafa gone or had serious doubts about him. It just needed 1 average season - 7th position and a EL Semi final - for a lot of fans to just want rid of Benitez. It was a really shite time to be a match going Red. Club was in turmoil and loads of people just wanted to pin it on the manager. It was a toxic around the club.
I don't think we are in that situation now. The club seems stable and 99% of the fans seem happy with Klopp. That's a big difference to where we were at in 2009/10 (with the benefit of hindsight).
In 2014/15 we weren't a million miles away from CL qualification. Though we finished 8 points off 4th we were bang in contention until the United defeat at home at the end of March. From that point will capitulated. We took 8 points from 8 games after the United defeat. With hindsight what we were witnessing was the beginning of the end for Rodgers.
In saying that I don't think the 14/15 squad of players was as bad as some people think. There was significant weakness at centre forward when Sturridge was unavailable but we still had the nucleus of a decent squad. I think that bore out a bit the next season under Klopp when we got to the EL and Carling Cup finals.
Whilst I agree with you that there was optimism still at the end of 08/09 and 13/14 about the future, at this point we seem in a much better place than either of them. The strength of the team may be comparable (or better) with 08/09 but the stability and strength of the club isn't. The club is in such a better position now and are primed for the next step. Where we stand now with the end of 13/14 isn't comparable either on or off the pitch. There's 1 definite and maybe 3 players at most from that squad who would get in the current starting XI. Probably only 4 or 5 who would get in the current squad. The club is in a better state from then as well.
Whilst no-one knows what happens over the next 3 games, next season or even beyond that, it's hard not to think that the club is in a good position to succeed in the future.