This win total argument is totally illogical, and I suspect that you know it. One team was intent upon finishing with as poor of a record as possible in order to secure better odds for a top lottery pick (gee, that worked out well). The other team was intent on trying to scratch into the playoffs so that its aging former-championship roster could try to give it one more go. Additionally, the roster I'm proposing would have one new starting caliber forward on it, so it's not the same lineup. Couple that with games lost to injuries last season for the Blazers' top players, and their win total from last year is nearly completely meaningless in terms of looking at the future. The only meaning it could possibly have is if you think it's indicative of the current top players are too injury prone to be relied upon going forward. I don't see that, personally, given that the injuries were not to major joints and ligaments and were likely exaggerated for purposes of holding players out of the lineup at the end of the season.
The roster that I would go into next season with would be:
C - Ayton (Williams, Reath)
PF - New guy (Walker, Murray)
SF - Grant (Camara, Thybulle)
SG - Sharpe (Murray, Rupert)
PG - Henderson (Brogdon, Blanton)
It could be that the new guy is a SF, but I'd prefer to go bigger with a better rebounding PF and switch Grant to SF. Some of the backups will no doubt be moved and new rookies will be brought in. With anticipated improvements to Scoot and Sharpe, and with the connection that was developing between Scoot and Ayton at the end of the season, I have zero doubt that lineup can contend for at least play-in spot and can grow from there.