Striker Luis Suarez's desire to leave Anfield in order to play in Europe's premier club competition and the Reds' failure to sign Shakhtar Donetsk midfielder Henrikh Mkhitaryan last month have only served to highlight the problems faced.
Gerrard has told the Uruguay international he wants him to stay despite two bids from Arsenal, but admits until they regain their top-four place they will always have to fight such battles.
"I think the only person who knows what's happening is Luis himself," said the England captain.
"He has a huge decision to make and, as his team-mate, I have to show him respect and give him space to make whatever decision he wants to make.
"But I think everyone knows how highly I rate him and how much I want him to stay, and what we can achieve this season basically depends on whether he stays or goes, I believe.
"While I've still got a couple of years left - and maybe a few more who knows - I have to make the most of it. And that is about adding more medals to what I already have and to leave this club in the Champions League. That is the challenge for me personally.
"It is not the same club (I joined) because we are not in the Champions League, so it becomes an awful lot more difficult to attract the top players.
"But I think the club's history and size - we've just been on a tour which has seen us play in front of nearly a quarter of a million people in 10 days - means the pull is still here.
"We need to break back into the top four to get back the pull we had four or five years ago when we were comfortably in the Champions League year in, year out and challenging to win it.
"Players who come and get the club back into the Champions League will experience some of the biggest nights of their career, because playing European football in front of this crowd is different to any other."
Mention famous Champions League nights at Anfield and thoughts drift back to December 2004 and Gerrard's late goal against Olympiacos, which put the Reds into the knockout stage by the slimmest of margins.
From there they went on to win the competition in a remarkable Istanbul final against AC Milan.
The 33-year-old rates it among his top three strikes and it is no surprise he picked the Greeks for tomorrow's testimonial at Anfield.
And while the occasion will celebrate Gerrard's 15 years as a professional at his only club - and a decade as captain - he insists the game holds greater significance as part of their pre-season.
"It's a bit surreal. Sometimes I have to pinch myself to realise how well my career has gone at this club," said the midfielder, who hopes to raise over £1million for his charitable foundation from the match and gala dinner afterwards.
"I'm starting to get nervous about the game. It's not about winning, it is because all the attention is on myself and I prefer it when it's on the whole team.
"It is still an important game because of the timing, with a couple of weeks to go to the season.
"I didn't want it to be a testimonial which was going to be low-tempo with all my friends and team-mates over the last 15 years coming back to play a part.
"I wanted it to be a serious game and it will be a serious contest."
On choosing opponents, Gerrard said: "Because of the timing of the goal, how important it was and what happened further down the line in Istanbul, that is the reason we decided to go down the Olympiacos road.
"If we were to have gone out on that night, this goal would never get mentioned. But because we went on to win it, when I look back that goal became very important to the club and myself personally - it's certainly in my top three goals I've ever scored.
"They (Olympiacos) have been fantastic and have not asked for a penny to come over and play.
"We spoke to a few other clubs who were demanding fees, so I owe them a huge thank you as it means more money will go to children in this area.
"This club and the game have been superb to me, so the least I can do is support the area I come from.
"I know I am not going to change the world, but if I can give a little bit back it will make me feel proud."