I think the real flaw in the strategy during this transfer window may, and I stress may, have been to over estimate the amounts achievable from the sales of Jackson and Nkunku. I say may because, until the window closes, we can't really know whether or not the club has accomplished what it set out to do.
It is possible that, had the club realised it might not achieve the necessary value from those sales it may well have reordered at least one incoming transfer. If the club genuinely saw Gittens as a higher priority than Simons or Garnacho then fair enough. If they miscalculated however, then that error is going to put our squad development back at least 6 months and probably more.