Not exactly sure you have any options to KIX other than via NRT from YVR. I mean I guess you could go via another country like Korea but I'd not advise since then you have another set of rules to mess with. Not sure many, if any, flight options to KIX from the US either directly.[heck, I'm not even sure who flies where now. Haha]

I recall the flights to NRT from YVR arrive around 4pm? So not many options for longer.

Maybe post the times.

Will they be in Osaka working or somewhere else?

How much time will they have before they start.

Unlike Canada, there are plentiful and convenient train connections between Tokyo and Osaka should one need to for many reasons. For example, spending some time in tokyo before?