This is projected to be a historical Draft. Watching very early season college film, Flagg, Bailey and Harper all look very legit. Traore and VJ also have looked very good at times and way above an average years #4-5 prospect.
Play the youngsters as much as possible. Find out what you've got. But any wins the Blazers get because of Ayton, Grant, Ant, Thybulle, Reath, etc is mostly a waste. Yes, the kids need to learn how to win, but they need to do it of their own volition. Help is on the way. Camara is already looking better. Sharpe was looking better in training camp until his injury (again). Scoot needs to show signs of improvement, you need to find out what Walker is, if Rupert will continue his growth curve, see what Kling Kong can do and if Avdija is a piece that can be a veteran to the youngsters, or is a trade piece for later.
Add to that a ridiculous bucket getter like Bailey (his ability to make shots is very advanced) an all-around playmaker like Flagg, a big floor general like Harper and this team starts to progress next year and the following year is a #6-8 Playoff team. By then, you have the future Draft picks you've traded for and whatever you got from Grant/Ant/Ayton/Thybulle, etc to add pieces to the foundation of your roster.
It will take time, but this year is the year to Draft that 'IT' player that propels them to the next level.