Aiming for end of 2022/23 season but there is a lot to take into account.
We need Ole's signings to all gel well quickly when they come in. We want to get Gomes to sign a new contract and we keep the rest of the youngsters and hope they progress at a decent rate. Some things could be disadvantageous Phil Jones contract is until 2023 with the option of an extra year, Smalling will be in his final year. Had a conversation with my mate and he reckons we will nothing until they are gone, so preferably one or both plus Rojo will be gone by next summer, sincerely hope he is wrong as he's a City supporting WUM but knows a lot and sometimes talks sense when he is not WUMMING me.
A plus is Matic' contract expires next summer so he will be gone hopefully, really hoping Woody doesn't give him any extension. Hopefully, Darmian goes this summer but his contract is up next year so he will be gone. When they go we need Woody to fork out the funds to replace them, he may or may not do, if he doesn't splash cash I think we are going to find it difficult. We are going to need Woody to get signings in quicker starting next season so they get more time time to get used to Ole's methods and gel, which I think is a massive point.
We are going to need each signing which comes in each window to do well and fit in quickly. At the end of this season, I would like to see us claim a Champions League spot by finishing 4th not by winning Europa League but would take winning Europa as a bonus on top of finishing 4th, it would get the younger players used to winning things and breed a winning mentality in the squad. Lingard has 2 years left so hopefully he will be sold but I've read which could be complete bollox that he is getting extension bumping his wage from £75,0000 to £130,000.
We need to hope the players respond well to Ole's tactics and are capable of keeping up his high-intensity game all season. This year we should be aiming for top 4 and maybe win League Cup to get youngsters used to winning, as I stated before, a decent F.A cup run although this is not essential with a stroke of luck win Europa League, whilst cutting the gap to the top 2 by a few points. Next season we should be aiming to comfortably qualify for Champions League pushing Spurs for 3rd place and hope to not get embarrassed in Champions League and maybe win the F.A cup luck permitting, whilst further cutting the gap at the top.
If we keep progressing, get rid of deadwood, replace it well and hope new signings are of required quality and gel quickly, the youngsters progress well as they will be in their third season around the first team, which I hope a lot will be starters by then, I think we will be ready to challenge for the League that year but there are a lot of if's and hopes. But by then I think we will have a good chance.