The part you’re missing in your assessments is money. I think that each year we have covered the top three or four priorities. That’s about what we have the money to do. There have been other needs but they are secondary.I find it very hard to believe that Ancelotti requested a complete lack of cover in several key areas.
For example, this season we decided to go with two right backs, but Coleman has suffered injury and JJK was injured / not good enough. We decided to give JJK a go and didn’t sign Sidebe. We tried to make the space for a younger player but it didn’t work out. We didn’t have the money for another right back. Simples. Plus we avoided Sidebe on a long contract. We can fill the place properly this summer, rather than having another average player on a long contract.
This process is painful now but better in the long run.