The Leafs were never trading JVR and Bozak after they made the playoffs in 16-17. They were one of the few veterans on the team at the time and it was also part of the reason Marleau was brought in.
Everything you're complaining about is because of hindsight. That 17-18 team? They had 105 points largely on the backs of their young players. That's not a team that's rebuilding anymore, especially after making the playoffs the previous season.
It's hard to say what Lou wouldn't have/would have done if he stayed on longer. I am pretty confident Tavares would not have been a Leaf if he stayed though. Lou does not have a history of giving mega dollar contracts in UFA. Marleau is actually his biggest in terms of cap hit straight from UFA.
I was aware they weren't going to trade JVR and Bozak. The TML management and the TML fans are a perfect match made in heaven because they are the exact same overly emotional, inconsistent, impulsive, impatient bunch and this is reflected in what the fans demand and what the management does. Then the fans turn around and start complaining about the management. There is no better fit in the world of sports than the TML management and the TML fans. It's some manifestation stuff.
None of what I'm complaining about is hindsight. I had a different account on here or else I would show my posts if I could still find them. Some of us had the foresight to see that other teams like Chicago and Penguins had done a proper rebuild from scratch with elite pieces supported by a strong supporting cast and didn't gung-ho crazy at the first smell of success. Some of us knew that we begged for a rebuild for ages and it would be hypocritical to turn and want to abandon what we craved for so long so early because we got in our emotions again. All of us knew this constant re-tool was not the answer and we had to go all the way for a rebuild. The problem is that's what the management promised, and that's what the fans claimed they wanted. Then neither management nor the fans had the willingness, maturity, or patience or whatever you want to call it to actually stick through with what they claimed they wanted. None of this was hindsight for me and lots of others - it was simply being mature and patient enough to know that team that faced the caps was never going to win and it would be a much better strategy to focus on our original goal. When management was questioned on this, there was a plethora of quotes coming from management that basically summed up to - YOLO! Yolo is what got us in this mess for all these years and why we wanted a proper rebuild yet everyone decided to go right back to it as soon as we had a good regular season. Stuff like "we never know what will happen next year and you never know if you'll ever get to compete for a cup again" etc etc was common to hear from Shanny/Lou/Mike.
In the case of what you're saying, the Lou of Toronto was clearly a different animal than the one in New Jersey. If he gave a 37 year old Marleau a SIX MILLION THREE YEAR contract you can bet your backside he would chase after a 27 year old John Tavares when on paper that contract at the time appears a lot better than the Marleau contract at the time it was signed. This is why I can't take these criticisms that hate Dubas but excuse Lou as anything but some kind of bias because Dubas comes across as a nerdy looking leftie. Because he merely continued the rushed rebuild that his predecessor started. You can't apply the principle that Dubas shouldn't have bolstered a good offensive group for leadership and depth and Lou wouldn't do that when Lou did exactly just that. I hated not trading JVR and Bozak, I hated the Tavares signing, I hated acquiring Boyle, I hated acquiring Coastleau. By the way at the time of the signing there was almost complete consensus that Tavares was a good signing on here - at least 80% of posters seemed happy about it and when pushed back asking why we should abandon what we wanted to get away from i.e. chasing high profile UFAs in the latter stages of their career constantly on over paid contracts especially this early in a rebuild rather than as a final piece for a team that's proven it can succeed in the playoffs, the response was met with "you don't pass on a player like this when available". If you hated the Tavares signing, which I doubt because most here didn't, then by the same principle you should have hated the Marleau one.
At the end of the day, nothing about this team will change because the fanbase will attract a management that is exactly like it and people who aren't interested in seeing something through are less likely to succeed.