Given the lack of multiyear contract given out by this front office, it's a better conclusion that the front office is the issue in not getting him signed.
I agree with your assessment of the Escobar trade. But it also describes the reason it was a bad trade. They underestimated his value. They lowballed an offer and ended up trading a valuable player that would have helped them the next year. Maybe they didn't believe the team could contend the next year so they were in rebuild mode. But just like the first year at the trade deadline, they misjudged the team.
Based on what we know, it sure looks move likely he wanted to stay but the FO chose to trade him. It was a mistake so far unless they get some production from the prospects.
https://www.mlb.com/cut4/eduardo-escobar-posted-hilarious-tweet-after-trade-c287663154 Based on his response, I don't think there is much evidence Escobar wanted to leave.
https://www.fangraphs.com/statsplits.aspx?playerid=12155&position=OF&season=2019 Also the wRC 148 in High Leverage situations and 131 wRC with Men in Scoring position. He came up big in the clutch and I think that is missed in the overall 103 number.
Their actual first year with Molitor when they went to the playoffs really set back their rebuilding plans. But they did a great job last year to get back on the rebuilding track.
https://www.forbes.com/teams/minnesota-twins/#3c10bba43bae Forbes had the Twins making $14 millions in profits last year which was one of the lowest in baseball. Revenue will be up and they can clear payroll to sign a big name pitcher, but I don't think they are as profitable as people like to believe.
'87 & '91 were pretty nice Injuries always happen, which is why teams need depth. According to reports, they have a loaded minor league system, so this is a test for the front office on how they handle this.