I would do exactly as you mentioned , I would not start the bike and drop the oil on a cold motor. Refill with ether Redline 15/50 powersports or Maxima extra 4T 15/50. Run that for 500 miles then drop and refill again , safe to run these oils every 2k from there on. This motor sheers oil down very fast. Especially 50W oil as it sheers faster.
Typically id say about 1/4-1/2 quart stays in the system from the oil cooler and passages of the motor. Put it this way after you drop this 300v and swap to redline , the next change you will see green in your oil from the remaining 300v.
if you really want to get down to being sure about whats going on in your engine , do an oil analysis with Speediagnostix . Id actually be very curious to see a 3000 mile sample of 300v and what it looks like viscosity wise.
https://www.speediagnostix.com/shop/p/standard-drain-sample-kit