I can't speak for any other team in the league, but I can describe what I've witnessed as a pattern of behavior for the Blazers over the last 15-20 years, particularly after the reign of GM Bob Whitsett.
"Trader Bob", as he was called, inherited a solid but aging team when he arrived in the late 90s, stuck in the tidewaters of a failed championship run 5 years before. Being the architect of the mid-90s Payton-Kemp Sonic Teams that challenged for the championship (and a former NBA Exec of the Year), he was given instructions by Paul Allen to reform the team into a title contender. He was not shy about taking risks, bringing in Damon Stoudamire and Rasheed Wallace, and ultimately Scottie Pippen, which immediately blossomed into WCF runs in 1999 and 2000. Emboldened by his sudden success. he swung for the fences.... and struck out. Bringing in Dale Davis, as well as Sonic retreds Shawn Kemp, Detlef Schrempf, and Reuben Patterson, blew the fragile chemistry of the team to bits, and resulted in several years of sub-.500 basketball and a strained relationship with the fanbase causing threats of selling/moving the team and defaulting on the ownership of the Rose Garden arena. New Management was able to slowly build the team back to respectability through the draft, but never making the drastic trades that would be necessary to raise the team from "solid playoff team" to "Championship Contender", which could also backfire and cause the team to regress.
It's my opinion that after the experiences of the mid-2000s where the team saw attendance and revenues shrink to the point of endangering the economic stability of the franchise, the team will never again take those kinds of risks. They will be content with being competitive, and catching lightning in a bottle occasionally as they did in 2019, but remained on a steady, "don't rock the boat" trajectory that would continue to see the team make the playoffs, occasionally secure first round home court advantage, but never join the elite teams that compete for titles year after year. A prime example was earlier this year when an MVP-type player became available in James Harden and the team made no realistic attempt to bring him on board, which would have cost the team core pieces of its existing squad, and would have created an unknown outcome. The team wants no part of "unknown outcomes", as they are deathly afraid of losing what they have, not just from a player personnel standpoint but also a profitability one.