Hi Blahness,
I will stick to the situation of making a 2nd ball flick and being ready to follow up attack... since I think it is one of the original situations you proposed.
... However, even if I chiquita or loop first, if the opponent is fast/stable af on the block/counter game I'm always a bit too slow for my liking on the subsequent shots, and eventually they get the better of me. The only way I win usually is if I overwhelm them with the amount of spin/power that they cannot handle. But past a certain point you can't expect them not to come back consistently.
So I can do decently spinny powerful loops on both wings, but what I'm lacking is the smooth connection between both wing to loop continuously and be in position no matter where the opponent places the ball. I have a bag of balls and multiple training partners, what drills do I do to improve this aspect of my game?
What is important is to make your shot, find a get to get to a ready position, and expect the ball to come back... and be neutral ready and seeking to follow up attack.
This comes from a good recovery and ready reset. As a right handed player, often on serve, you are stepping in with your right foot and flipping (unless ball is to BH sideline)... one way to reset quickly is to practice striking the ball... and very shortly after the strike, push off with that right foot.,, and get a jump step going that is opening up your hips... so that when your right foot lands, you are in open FH position... then you can take another hop or step to get to the next ball.
Keep bat waist to belly high and finish with bat on side and a bit in front.
This stance and postion will let you quickly get to the next position.
If you were watching your shot or not efficiently recovering crouched in open hip position, then it is very difficult to move effectively again.
Many shots in TT are missed or are much lower percentage from poor movement, poor position, poor balance/stance/leverage. Getting this right lets you see the ball better and it is a simple thing in TT. Every shot has this happening well or poor.
It may sound stupid to practice your in and out step with a fake impact (when you are by self) (and later with partner giving you short ball to flip and a 3rd ball counter), but it will help you out a lot.