I requested to upgrade my facilities in February of my in-game year. We are currently in October. I was told that the work would be completed by the end of the previous season.
It currently says Planning (completed 18/05/2038) however my facilities are still on Excellent and I no longer have the option to request upgrades to either my youth facilities or my regular training facilities.
I have nearly 200m in my clubs bank so I definitely have enough funds to cover expenses.
I seem to remember receiving an email stating that my facilities had been upgraded from Grade 2 to Grade 1 and that in turn I would need to hire new staff to cover something, but the email definitely didn't tell me which staff to purchase or how many of them. I've overhauled my backroom since then anyway and still nothing has changed