I think Addy covered it. My husband and I tried the Indian Arm last year as an out and back from Squamish. The bridges have been taken out and there are some challenging crossings. We turned around at one of the washed out crossings before making it to Indian Arm, but if you had the time and desire there should be plenty of logging refuse to create a makeshift bridge. The Sea to Sky Trail--esentially the Cheakmus Challange-- is a good ride all the way to Whistler once you are in Squamish. I heard that there was some work done on the trail near the top of Paradise Valley. The ride up Highway 99 from North Van to Squamish really isn't bad....
The other ride we considered but didn't get to this year is to ride Whistler to Pemberton on the highway and where possible the Soo Trail. Once in Pemberton take the FSR to the Skookumchuck hot springs. The FSR then connects into the backside of Harrison Hot Springs. Once at Harrison, you could ride Higway 7 back into town.
Have fun!