Balancing the Passage of Time

I've discovered that meshing together the passage of time for two different points of view is a huge challenge (another reason NOT to use more than one POV). Some ways I usually show time in my writing include:

1. Directly mentioning the day or time of day, e.g. On Tuesday....

2. Including brief sensory details to help orient the reader, e.g. fire sparking in the night; smell of coffee brewing, etc.

3. Using the weather or seasons, e.g. mentioning different weather from the scene before suggests time has passed.

These tricks might work this time, except that I have a problem. I'm mostly following the main character's timeline--she's in a contest and there's lots of tension about meeting the challenges of the contest. There isn't a lot of flexibility to her timeline. I can't stretch it out too much or it wouldn't be believable. Unfortunately, my second point of view character needs time. He's adjusting to a whole new life. Sigh. It's hard to weave it together.

So far, my strategy is to stick with the timeline for the main character and try to fit the secondary character's POV around it. But it's created a challenge for me I hadn't anticipated. Have you ever encountered an unexpected writing challenge? How did you make it work?