quick turbo and trans shift general question

[Brickhouse]

Hi Everyone, Two questions.

1- Do I have it correct that when the turbo starts occasional chirping, it's starting to die?

2- Ever cense the trans was done, 90% of the time, the overdrive when it engages, the engine "flairs up" a bit. Like it's having trouble engaging? Sometime, goes right in. Happens under acceleration, and easy steady speed. If I let off the throttle at the right time, it engages ok without the flaring. Not sure what's up, and if it's going to cause mechanical problems down the road.