Planning to make Strong Scotch Ale and target OG is 1.085, and yeast is WLP028. My plan is to boil 2 pints w/0.5 cup of DME and pitch yeast in my 1000ml flask. I'll let sit (well will stir occassionally) for 24 hours, give or take. My questions...
1. WIll I have issues with the 2 pints being just under the narrow part of the flask?
2. If not, will that give me a sufficient yeast count? Or should I just buy another vial?
Assuming a batch size of 5.5g and 2 week old yeast, you are well under. It also appears you are not using a stir plate, but rather agitation. If I'm correct on all this, then you will be at ~188B cells, and need 319. With a 2nd vial you would come closer. See the calculator on Brewer's Friend. (and build a stir plate!)
As for flask size, that's close, but should be ok. I have a 2000ml flask for my starters and have never exceeded 1.5L.