Although the rise of Bournemouth and Brighton has been powered by smart recruitment, Everton are still refining their transfer approach.
Under former owner Farhad Moshiri, eight players who cost at least £20m departed for nothing.
After years of tighter spending, the Friedkin Group signed nine players last summer, but the youth-led strategy has yet to pay off.
Grealish and Dewsbury-Hall have delivered, yet 20-year-old winger Tyler Dibling has made only six starts since his £35m move from Southampton.
Young left-back Adam Aznou, who arrived from Bayern Munich last summer, is still waiting for his Premier League debut.
Striker Barry, 23, won more aerial duels than anyone in his first Premier League season but lacked consistency in front of goal.
Midfielder Merlin Rohl, 24, struggled for minutes early on before impressing with four starts in May.
BBC Radio Merseyside’s Giulia Bould reports the influential Grealish is likely to return on loan late in the window as he continues rehab from a foot stress fracture.
His wages are expected to remain around £200,000 per week.
Meanwhile, Iliman Ndiaye has been linked with a move to Saudi Arabia.
“I’d welcome Grealish back, but only at a price that suits Everton,” says Osman, who made his Everton debut under Moyes during the manager’s first spell in 2003.
“With Ndiaye, I’d hate to lose him. There could be a fee that makes sense and lets Everton reinvest in two or three players, but they should do everything possible to keep him.”