"There's lots of money floating around in amateur football in New Zealand. It's a bit crazy, really."
Some players, he says, in teams such as Miramar Rangers pocket decent money to ply their trade.
"You think, 'Jeez, when do you stop getting six, seven, eight, nine 10 players in each year to look after the club before they go away again'.
"That's the same with Hawke's Bay United and a lot of franchises which aren't local any more."
He says Team Taranaki's demise poses the question: "When do we start becoming sustainable?"
The ensuing question pertains to building a reservoir of youth talent to carve a better pathway.
The Wanderers' have close to an identical squad from the one he coached last winter in the winning lower-tier Lotto Federation League campaign.
They have lost leftback Liam Carrington to Otago University in Dunedin.
"We're still working on our squad and we're just three-and-a-half weeks into Central League now, to be fair."
It goes without saying Greatholder has immense respect for the standard of the league and the experience of players and coaches.
Havelock North, he says, have a fair way to go to acquire that threshold in bridging the gap from where they are coming from in the winter hierarchy.
"Are these players good enough now to play Central League level?"
Greatholder is keeping the faith in them even though they may have to cool their heels for a few years to ensure a cluster of teenagers become more soccer savvy.
"It's the mentality, both on and off the field," he says.
No doubt, staving off relegation from Central League is the challenge to become a sustainable side on the foundation of a "great youth policy".
It is, without doubt, a two-edged sword so clubs, teams and coaches are bound to wince either way.
"Obviously we got a call about three weeks or so back and we thought, 'Okay, let's have a good go at it', so it's a privilege and opportunity and it would be silly not to maximise that."
Greatholder cannot offer names just yet but the Wanderers are looking to sign three players late next week but not too many where the villagers start losing their sense of identity.
A rash of pre-season matches has provided a laboratory for experiments to mould a template of sorts to refine their tactics and shape.
As the coach he isn't shy to put the acid on his boys to stake a claim.
Radicalism has taken hold of the way the villagers will approach Central League in the belief they have the balance to achieve that.
"It's a massive test for me as a coach if we can get our tactics and shape right to try to out-fox the opposition, if you like, with a less talented squad," he says.
Of his squad of 20 so far, all bar one is from the Bay but the trio to come will be a mixture of Kiwi and imports.
The Englishman considers himself a "local" after 13 years of residency and believes so do others who fit that mould.
Goalkeeper Nicholas Hayward, of Levin, comes into the fold from Team Taranaki to provide some competition for veteran Shaun Peta.
Kenneth Willox is an Englishman in the side that has Ethan Dent as captain.
Dion Adams will assist Greatholder and Bruce Barclay, who also is club president, will help.
Essentially, he sees it as Wanderers needing to beat one team to prolong their status in Central League.
"We will, as a club, get stronger next year and the year after that. At what level we'll be playing will depend on what we do this year."
While they missed out on Central League promotion on aggregate goals on home-and-away matches to Integrated Works Waterside Karori in August last year, Greatholder says their fellow newcomers also have spent money on signing overseas talent. He was aware of at least an American import in their squad.
"I've got to admit I'm getting back to that level of football where my feelers haven't been too busy. Three years ago I would have told you every player across New Zealand and all their strengths and weaknesses when I was a national league coach."
While it was "quiet behind the scenes", he emphasises gone are the days when oppositions could tick off boxes on two or three teams at the bottom of the table to target for three points.
"I reckon there are seven or eight sides who fancy their chances of finishing on the top couple [of rungs]."
Rivals may see Havelock North as easy pickings but Greatholder says his troops will obviously try to have a say on that.
A former Central League-winning player with the Blues, Greatholder needs no reminding how tough a grind it'll be when they embark on their journey to Stop Out on Monday morning before returning around 11pm that day, with lads having to go to work on Tuesday.
It'll be away to Newtown Park to face Wellington United the following Saturday before they host Miramar Rangers on Sunday, April 15, in a 1pm kick-off.
"It'll be brilliant to get Miramar to little old Guthrie. If we get a couple of beatings along the way, so be it, because we'll get stronger each week."
Work is under way to upgrade the Guthrie Park clubrooms.
"We have had a few sponsors who have knocked on our doors to ask if we need support so the story is good."
Greatholder is mindful people realise Havelock North are trying to create something special in putting some faith in homegrown footballers.
"We're not talking about massive bikkies here, unfortunately, but it'll help us out and, hopefully, get people out here to watch us and buy into our story."
The last time two Bay teams were in the Central League was when Greatholder-coached Maycenvale United beat Team Taranaki in 2011 to compete the following year with the Rovers before bowing out.
The Wanderers have had a rich history in footing it at Central League, dating back to the 1970s when it had three tiers. The Blue and Golds worked their way up from third division to second before gaining promotion to the premier Central League in 1987. They gained promotion again in 2004 and this winter it'll be their third representation.
The other Bay team to compete in the Central League were Taradale FC.
Fans in the province often say when there is more than one team in the league it's often an indicator that the province is teeming with talent.
WANDERERS SQUAD
With shirt numbers:
1 Shaun Peta (GK), 2 Christopher Greatholder, 3 Tuhiwai Kennedy, 4 Campbell Whitworth, 5 Stefan Kitching-Nicholson, 6 Kurtis Maney, 7 James Barclay, 8 Ethan Dent (c), 9 Jared Bloor, 10 Ben Foxall, 11 Harry Fautley, 12 Kenneth Willox, 13 Oliver Chapman, 14 Brad Calder, 15 Sam Waddington, 16 Jackson Ralph, 17 Liam Shackleton, 18 Guy Reeves, 19 Che Jesson-Bentley, 22 Nicholas Hayward (RGK).
Coach: Chris Greatholder
Ast coach: Dion Adams
Ast coach: Bruce Barclay
Manager: Tony Simons
Physiotherapist: Colin Tutchen (Focus Health)