Mike, my wintersown seedlings all go from the milk jug right into the ground.
To do this I dump the whole blob out of the jug, then cut into squares with a kitchen knife. Size of squares depends on how heavy germination was and the time I want to spend. Then I just plant into the garden bed.
I think the problem with "potting up" to small pots might be keeping them adequately moist. That's no easy task when hot weather arrives unless the pots are a pretty big size.
Mine (lobelia cardinalis) have just formed basal rosettes in the first year and started blooming in the second year. That might vary according to your zone + climate but for me it's second year.
Karen