I think Lindsay and then Whelan were struggling to adapt to the SL era and the rise of Bradford and Saints and were acting like those presidents of the galacticos European football teams who like shopping for players and changing coaches in the hope that something works. Halifax had a great season in 1998 and were the team on the rise, so their best players Florimo, Chester and Clinch turn up at Wigan. Orr was the rising star at Cas, so they get him in. Moran was a one-man team in London, so they get him in.
It was a strategy that kept Wigan trapped just below the top tier, they had a rotating door of talented players who came in and out but they didn't have the stable core that Bradford, Saints and Leeds did, other than Farrell, and when he left the foundations caved in rapidly. It was similar to the Sydney Roosters in the 1990s (when Lam was there), they were the 'transit lounge' for big names coming and going then something clicked in the early 2000s when Ricky Stuart was coach and they dominated the NRL for a while.
In the 2010s Wigan had a different approach, much more strategic, no vanity signings, mostly a home grown core and then some signings strategically bought in. Some of these, Blake Green, Matty Smith, were like Clinch in that around the league people thought is this guy really a Wigan calibre player, but they fit the team and what Wane was trying to build.
I remember early in 2004 seeing an interview with Mike Gregory when he was hinting at changing the culture in the direction of the type of thing Wane would later bring in - moving away from big names and big egos towards building the squad around the generation of talent coming through. Obviously tragic events intervened but if that hadn't happened, it would have been interesting to see if Whelan would have had the patience for MGs approach. He soon reverted to type, bringing in Millward and then going on that big recruitment spree for 2006 which completely tanked.