Spending unwisely for more wins has been the problem with the Raptors since their Carter days. It was only slightly more justifiable in Grunwald's days. Now it is totally unacceptable. Spending more money to put a 45-50 win team on the court for 2-3 years with no plan to make the team better beyond that is crappy team building. I would rather win 40-45 wins and maintain as many options to make a significant jump to a 50 or 55+ win team within 3 or 4 years instead of at that time struggling badly to keep a 45-50 win team from falling apart and getting worse, or having to rebuild again.
You would be building the team around 3 guys who have never made an all-star game and pretending that's a competitive core. Lowry has done nothing to convince me he's worth keeping. Gay is certainly a good SF, but if he's the best player on the team, how good is the team? And Millsap is a solid PF, but again, he is not spectacular in any way. He is a good post player and rebounder, but isn't elite in either way, nor is he someone you can play as a shooter. He can shoot, but you wouldn't just use him as a stretch PF, it's not his game. You would be building a team that would be lucky to make it out of the first round for however long they're together, where any improvement would still depend on JV's development. And if that's the case, the focus from now should be on having the team built around JV, instead of having to change trajectories in 3-4 years. And the more they build the team for winning now (or rather for the next 2-3 years), the harder that becomes.