Cool. It's always good to test to be sure. Things can often depend on the wood, humidity, etc.
But you're results echo mine exactly, at least on oak. I found that starting with red oak yielded a little darker/redder color than White oak.
If you're staining pine, definitely use a conditioner (unless you're shooting for that blotchy look, which, in some cases might be appropriate).
To me, it seemed when I put down a second coat of stain, the second coat kind of "melted" the first coat, and the color sometimes would even get +lighter+
I did experiment with literally "painting" a coat of stain on, really heavy, then letting it dry completely without wiping it off at all. I got the darkest color out of it and believe it or not, it looked pretty good once I'd hit it with some very fine steel wool, removed the dust and clear coated it. Yeah, technically not how you're supposed to apply stain, but I got the color I needed. Just let it dry completely, like for a week or so.