After all, the Blues boss, unlike his predecessor Jon McCarthy, does not have the luxury of a significant chunk of the Sam Hughes money to spend.
The sale of Hughes - for an initial fee in the region of £130,000 - was a good deal for the club.
The same, though, cannot be said of two previous players who made the step up into full-time football...
Danny Williams and Ben Heneghan
I'd never seen Neil Young so furious. His side had just wrapped up their Conference North title-winning campaign, but the only thing on his mind was the impending loss of Danny Williams.
Chester's failure to wrap up the permanent signing of Williams for a nominal four-figure fee came back to bite them when Kendal Town sold him for a far bigger fee to Inverness Caledonian Thistle.
The flying wingback spent three seasons with Inverness, winning the Scottish Cup, playing in Europe, and reaching the Scottish League Cup final during that time, before moving to their Scottish Premiership rivals Dundee.
Now, following his release from Dundee, Williams has signed for League Two promotion pushers Accrington Stanley.
And the 29-year-old has been joined at Stanley by young Derby County striker Offrande Zanzala who, of course, spent a spell on loan at the Blues earlier this season.
Heneghan, meanwhile, has been linked with a switch from Sheffield United to Rotherham United.
The centre-back, who Chester did not receive a penny for after his move to Motherwell in June 2016, only joined the Blades during the summer.
However, Heneghan has yet to play for the Championship promotion hopefuls, and he is now being tipped to join League One Rotherham on loan.
One player the Blues will - eventually - get compensation for is striker James Alabi.
But his future, at the time of writing, is no clearer.
It was reported last week that Alabi was to leave loan club Dover Athletic and join Ebbsfleet United from his parent club Tranmere Rovers.
Now Dover boss Chris Kinnear has had his say on the saga.
He said: "It's down to Tranmere, Ebbsfleet and the FA. We aren't sure there are letters going around all over the shop. He has left us and made that quite clear.
"He just didn’t turn up for training one day. That's football and you just move on. We will try and get other players in.
"We weren't told and there were pictures of him going to Ebbsfleet. We find out after the pictures are in the papers.
"It didn't quite work out for him here and whatever he does in the future good luck to him. He's a nice lad and we wish him all the best."
The Blues welcome Gateshead to the Swansway Chester Stadium on Saturday for another crucial clash (3pm).
And the Heed will make the trip without Luke Hannant as the star midfielder has joined League Two Port Vale - and his previous manager Neil Aspin - for an undisclosed fee.
Hannant's last contribution before leaving was scoring Gateshead's winner in their FA Trophy replay in midweek, which did much to boost the confidence in Steve Watson's squad.
Heed boss Watson has responded by signing 18-year-old striker Lewis McNall from his former club Newcastle United and 19-year-old midfielder Ben Fox on loan. Both players could make their debuts against Chester.
Wrexham signing and Hartlepool to be paid
Wrexham have bolstered their forward options by signing Blackpool forward Scott Quigley on loan for the reminder of the campaign.
Quigley joined the League One Tangerines in the summer for a fee rising to £50,000 from Welsh Premier League champions The New Saints.
The 25-year-old could make his Dragons debut on Saturday at Hartlepool United, the crisis-hit club who are managed by his ex-boss at TNS, Craig Harrison.
The good news for Harrison and his players is they are set to be paid next week - after their trip to take on the Blues on Tuesday (January 23).
That has been made possible thanks to an online fundraising page set up by supporters that has raised more than £50,000.
The fact that the clash with Wrexham is a 7,229 sell out will also help matters.
But, while the threat of administration may have been staved off for the short term at least, Harrison will not be able to extend the deals of Jonathan Franks and Keith Watson.
The Dragons, meanwhile, have released Ferdinand Takyi following Quigley's arrival.
Relegation rivals strengthen
Another week, more new faces for the teams battling with Chester down at the bottom.
Guiseley have extended the loans of striker James Roberts - who once had a spell with the Blues - from Oxford United and defender Adam Crookes from Nottingham Forest as well as completing the permanent capture of young Burnley defender Harry Flowers.
And there are reports tonight that Guiseley, whose match at home to Barrow AFC tomorrow has been frozen off, are about to sign former Republic of Ireland international defender Sean St Ledger.
The Lions are, though, on the verge of losing goalkeeper Jonny Maxted to Accrington, who were impressed by his performance in the FA Cup meeting between the sides earlier this season.
Solihull Moors have splashed the cash again, this time for defender Tyrone Williams from Kidderminster Harriers, as well as bringing in Bristol City teenage midfielder Opanin Edwards on loan.
Moors, though, could be about to lose forward Oladapo Afolayan, who is a reported target for Derby County and Birmingham City.
Torquay United have done a loan deal for Dagenham and Redbridge frontman Elliott Romain while Barrow, whose manager was far from happy in the week, have signed ex-Gillingham keeper Steve Arnold on an 18-month contract and attacker Luke James on loan from Forest Green Rovers.
Best of the rest
Lincoln City defender Callum Howe was a player McCarthy is understood to have passed up the chance of signing in the summer when he was still in charge of the Blues.
Howe went on to join Eastleigh on loan, where he has played 26 times, captaining the team on 16 occasions, and scoring three goals, before he was recalled by last season's National League champions Lincoln earlier this week.
"He's been great, in the last couple of weeks especially," said Eastleigh manager Andy Hessenthaler, who has signed young Bristol Rovers midfielder Ryan Broom on a month's loan.
Macclesfield Town are looking like the team who will follow in Lincoln's footsteps and win the league.
And Macc are certainly not resting on their laurels with the signing of striker Nathan Blissett on loan from Plymouth Argyle, along with defenders Callum Evans and Adam Dugdale from Forest Green and Southport respectively.
Oldham Athletic's Mason Fawns has made a loan move to AFC Fylde, who have allowed fellow midfielder - and one-time Blue - Tom McCready to join Colwyn Bay.
Maidenhead United - Chester's host on Saturday week - have secured a fresh loan spell for attacker Moses Emmaneul from Sutton United.
Joe Pigott has made the leap into the Football League with AFC Wimbledon after scoring 12 goals for Maidstone United this season.
Aldershot Town have re-signed Forest Green Rovers midfielder Fabien Robert on loan, Woking have snapped up Reece Grego-Cox after his release by QPR but lost fellow striker Inih Effiong to the Scottish Premiership's Ross County, while Bournemouth defender Ollie Harfield has joined Boreham Wood on loan.