OK, so came up with a few options. Thoughts?
Option A 21x34 front and rear entry.
Probably the toughest at this point given the alley entry, unless I can get the city to substantially raise the grade. Drawback is the front would have to get the level far enough down for the back to be flat.
Option B 22x32 rear only
Probably my least favourite option because the front drive is unusable to access the garage. The alley isn't great in the winter and my wife probably wouldn't like having to use it.
Option C 22x32 Front only
Requires a bit on manoeuvring for the right side parking spot, but not to bad. Lots of extra driveway needed between house and garage.
Option D 21x34
Came up with this brilliant one last night. Would require a bit of a retaining wall, but becuase the drive is coming form the uphill part of the alley, the grade shouldn't be unmanageable. I still need to do some checking to see if this would work. Not sure if the city would let me have a small wall past my property line, but could probably make it work ending at the line.
Drawback is loss of a bit of that corner of the yard. Also, interior configuration isn't as optimal, but I could use the space between vehicles for bike storage and still have a large are for a shop.