With Paul Groves and David Coles leaving for West Ham, the new Pompey manager now has to recruit more backroom staff as well as a whole load of new players.
The staff issue isn't so much of an immediate problem as John Keeley has been promoted from the academy to become the new goalkeeping coach, whilst Ian Woan and Guy Whittingham are still at the club.
However, one look at the current squad list simply underlines the monumental task that Cotterill has.
We currently have a squad of 25, yet that doesn't count those players who are out-of-contract or are certain to leave. Take those players away and you are left with a squad of around 14, and that includes youngsters.
Steve's main concern is that he can do nothing to rectify this situation until mid-July at the earliest, he can't sign players (and when he eventually can he can't spend any money) and he has to watch his best players walk out of the door.
This is a similar situation to last season, isn't it? Last year all of our remaining stars abandoned ship and we were forced to cobble together a load of players borrowed from other clubs and those who were unwanted.
And whilst these players managed to get us to an FA Cup Final, we also suffered a terrible league season which ultimately ended in relegation. Given the parallels between this pre-season and last, you can't help but be worried that the same is going to happen again this season.
But despite this, there are some positives to take from the situation in that I believe that we have the right man to build a new squad from virtually nothing.
If he can keep the nucleus of the team together (meaning Rocha, Mokoena, Brown, Wilson, Mullins and Smith) then he can build around that and form a good team. If, in the unlikely event that we can keep hold of the two Davids in James and Nugent, then that would be a significant bonus.
You may be thinking that that's a poor pool of players to draw any sense of optimism from, but you have to remember that there are no Manchester Uniteds or Chelseas in the Championship. The standard is a significant drop down, a standard that our experienced crop of players, no matter how small, should be able to cope with.
I have a feeling that we may well start slow as our new recruits are blooded into the first team, but the Championship is an unpredictable league that allows teams to start badly but have a good season when everything is in place, something that the Premier League doesn't.
So whilst we may all have that feeling of déja vu at the moment, I have a good feeling that the end will be different this time around. After all, it can't be as terrible as last season, can it?