Opinions on 2nd Puppy Sleeping Arrangements

In 6 weeks I get to pick up Bentley's 1/2 sister. Bentley will be 9 1/2 months at that point and hasn't slept in his crate since he was 4 months. That first couple months crate use was critical to get him potty trained. He still sleeps in our room, we just shut the door so he can't roam the house.

Does anyone have any experience trying to put one new puppy in a crate while the other older puppy is free to roam around?