Would you do this? Am I wrong?

My toddler is having a really hard time with bed time lately. He is tired at the same time each night but I never allow him to get over tired. I put him down in his crib as usual. But lately he immediately stands up and cries softly or whines. He does this for a minute or two then lays down. He lays down for only 2 minutes or so and is back standing up crying (not screaming) or whining or asking for me or my husband (saying mommy! Daddy!). If I go lay him down or rub his back he SCREAMS and gets so upset he holds his breath. So I have bene letting this up down up down cycle go on while watching the monitor. Sometimes it takes an hour. Idk why this is happening but it's been weeks. Eventually he settles but wakes up an hour later crying and will not settle for the rest of the night unless he sleeps with me.

Is it wrong that I'm letting him quietly whine or cry? We don't agree with CIO but if I pick him up each time he never goes to bed. Also any suggestions on what the best thing to do in this situation is?