I have posted this tutorial on crossing the Strait of Georgia and you will get plenty of resources from it. I'll give the link below.
The last time I crossed the Strait of Georgia, I was coming home from the Vancouver International Boat show and I was on a BC Ferry. The beam sea and winds were nasty and the Ferry was getting slammed. Everyone walking around inside the ferry looked like drunken sailors, kind of staggering everywhere. It was also snowing out so hard we ended up in white out conditions.
Now having said the above, the most common problem in the Strait in the summer for sailors is no wind. In fact many joke that the wind dies at around 4:30 PM so that happy hour can proceed smoothly.
In the video, you will hear them talk about Qualicum Beach which is where I live. Yes it can get nasty out there, I love to sit in my car reading a book listening to the waves pound down at the beach. But it is also sometimes glass flat. As the webinar hosts say in many of their other videos, many locations in BC are not to be feared but to be respected. I would say you are wasting too much energy worrying about Georgia Strait.
If it were me personally with your time frame and your home port, I'd only go as high as Desolation and take a more relaxed cruise. One great way to get into trouble is trying to stick to an agenda.
I have edited this in. False Creek is a great place to anchor, you are literally in downtown Vancouver and great areas to eat and increase your girth, but you need to know about permits. I have just done a copy and paste for you:
A boat anchored in False Creek
Anchoring in False Creek is a great way to explore the city. You will be close to downtown Vancouver, Granville Island market, and some of Vancouver's best shopping, theatres, and restaurants.
Anchoring permits
Boaters need to get a permit to anchor in False Creek when they are:
Anchoring more than 8 hours during the day (9:00am to 11:00pm), or
Anchoring anytime between 11:00pm and 9:00am the following day.
Permits are available at Heather Civic Marina. They are free of charge.
The permit will allow boaters to anchor a maximum of 14 full or partial days of 30 days during high season (April 1 to September 30) and 21 days of 40 days in low season (October 1 to March 31).
Boaters may extend their stay in False Creek by moving to a marina after their allowable anchoring time has expired.