I set the trans on the trans jack, which is about the same height as the engine stand. Then use the picker to get the engine off the stand and roll the trans jack over to it. I work on it this way standing up and can tilt the engine and the trans independently any way I need to line it up.
I've also done it the way that Sirrotica mentioned, gently setting the rear of the oil pan on the floor, usually padded with a moving blanket, then wiggle the trans up to it on the floor. Works if you don't have a trans jack, I just find it a little more difficult.
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