The 'upwind' or 'downwind' sailing is pretty much the nature of BC.. the topography tends to steer the winds in a primarily NW or SE direction depending on the positions of the high and low pressure areas, and most of the mainland fiords and inlets (also narrow) often develop diurnal winds, blowing inland, often hard, midday and going the opposite direction overnight.
We get to 'reach' sometimes when crossing the Strait eg Gibsons to Silva, Pt Grey to Porlier, Comox to Powell River, but otherwise we tend to have to either beat or run, so we have to get pretty good at both unless you're willing to power through..
Those 'contrary' tides can be used in your favour with some careful planning and timing, and the tides and currents get fairly/surprisingly strong mid strait at times too, esp when the Fraser river is running hard.
From down south to Vancouver, Pt Roberts is a decent jump off point... Sucia possible.. also I think Cabbage Island on the Canadian side is a 'phone-in checkin point' that might also work for you. It would be a long day beating into an ebb to get to Vancouver from there, though.. the next few days are likely to have SE winds which would be great for you, but strong and wet by the looks of it.
Strait of Georgia - south of Nanaimo - Georgia Basin - Forecast - Environment Canada
Things look to get better by the weekend.. when we set of for 7 weeks or so!!
Once you get here, if you're not in a hurry to get north, take the time to check out Howe Sound too, Gambier Island has plenty of hideyholes, and the trip up the inlet to Squamish is gorgeous and the club there is welcoming (but you'll have to beat one way at least!)