No takers? Ok. I think either approach is equally valid, though very different.
1. We might call this "long arm Wing Chun." This is typically what the TWC guys do. Stay around that boxing/punching range, avoid the jab, work to the blindside and tie up one of his arms, pepper the opponent with kicks on the way in and punches when within range. Work at off-balancing him but not necessarily closing to any kind of grappling. The problem here is that a good striker can be hard to defend against. A good boxer with mobile footwork can make it hard to get to the blindside. Even though you are throwing some good punches, they aren't necessarily going to take out someone with a "good chin", so it may be hard to finish from here.
2. We might call this one "close quarters Wing Chun." This is typically what Chu Sau Lei Wing Chun does. Intercept what the opponent throws and close quickly to "trapping/clinching" range, move into the opponent to off-balance him and make him take a step while staying "attached" to him for control, pepper him with punches and slap on an arm-lock, neck crank, or choke as appropriate. The problem here is that a good dirty boxer or grappler is hard to off-balance and control. You have to keep him from clinching or tieing you up. You can very easily, and will very likely (!) end up on the ground from here. But with a Boxer, this isn't typically a problem.
#1 seeks to control the striking range and dominate there.
#2 seeks to control the trapping/clinching range and dominate there.
IMHO, too many in Wing Chun do neither one! At least not very well.
And it seems NO ONE is doing both well! At least not yet!