But, if neither factor is entirely under his control, Reid is optimistic about completing his Olympic dream.
Tackling first the potential club-v-country debate, a convincing case could be made that West Ham owe the man destined to be their next captain. After all, when the last Olympics were taking place in their own backyard, West Ham reached an arrangement with Reid that saw the centre back skip the tournament.
Reid was, at the time, about to begin his third season at Upton Park, with his spot in the team not as assured as it would soon become. And West Ham, having earned promotion from the English Championship, were plotting for a key campaign back in the Premier League.
While that agreement suited both parties, fast-forward four years and an Olympic place would see Reid's 2016 pre-season preparations occur on another continent, with a minimum of three matches in Rio likely rendering him an absentee for West Ham's opening fixtures. But for the sake of both his own ambitions and New Zealand's prospects, Reid hopes the faith showed in 2012 will be repaid.
"The last one that was in London," he says, "we made a calculated decision that it was more important for me to stay with the guys, have a full pre-season and make sure we got off to a good start when we came back up into the league.
"This time around, I think we can figure something out so hopefully I'll have the opportunity to take part in the Olympics. We'll cross that bridge as we get to it but it's definitely something I'll be looking forward to, trying to take part and lead it."
Reid has had few opportunities to lead his country of late, which is where the second question arises surrounding his Olympic prospects: West Ham, as is their wont, will release Reid only if he is fully fit when the international call comes.
The club's consent has recently been a rarity, with an injury bug biting the 26-year-old this season. If health woes plagued Reid's personal form as West Ham battled to retain their place in the top half of the Premier League table, then those same issues also severely restricted his international involvement.
In fact, in the nine months since Anthony Hudson took charge of the All Whites, Reid has featured just once under the new national regime.
After playing 90 minutes against Uzbekistan in Hudson's bow, injury forced Reid to withdraw from November's two-match tour to China and Thailand, before a hamstring strain produced the same result ahead of the friendly against South Korea in March.
While the cynical would cast aspersions on the severity of those ailments - similar to the doubts West Ham manager Sam Allardyce must possess regarding the benefit of such trips away - Reid insisted his intention, both past and present, was to wear the silver fern as often as possible.
"Obviously, I would've loved to have been in the past camps," he says. "But I've had a run of injuries and it's been one of those situations where I've had to manage it along the way.
"Even now I'm still picking up stupid injuries, so hopefully next year that will change and I can come back and participate in the games.
"I always want to come back and play. The main thing for me is to stay fit and have a good pre-season next year," he says.
Such a scenario is essential if Reid is to link with the All Whites in September's international window. And it's also imperative if he wishes to recapture the rhythm missing since the New Year which, if nothing else, is a matter of personal pride considering the level of investment West Ham made on his future in March.
The East London club, to be fair, hardly had a choice in handing Reid a six-and-a-half year deal worth a reported 60,000 ($121,000) a week, at least if the papers were to be believed. But despite having been repeatedly linked to Liverpool, Arsenal and Tottenham, Reid's future always lay with West Ham.
"From what I understood, there were no offers from any other club," he says. "We were talking to the club for a long time - probably a year before it all got sorted - but it was just one of those things.
"It takes time, really. There was no big drama to it or anything, and we're happy it all fell into place and worked out in the end."
The new contract will keep Reid with West Ham until 2021, which would see him register more than a decade of service, or enough time for a testimonial match.
And, having already made more than 100 appearances for the first team, the stage is set for Reid to write his name in club history. Not that the unflappable defender was preoccupied with that achievement.
"I just want to have a career here, make sure I put in a decent shift, and whether I turn out to be iconic or whatever you want to call it, it's not that important to me," he says. "I just want to be remembered that I always gave 100 per cent and just generally served the club."
NZ's over-age Olympians
2008: Ryan Nelsen, Simon Elliott, Chris Killen
2012: Ryan Nelsen, Shane Smeltz, Michael McGlinchey
2016?: Winston Reid, Tommy Smith, Marco Roja
