Mesic woodland.
Most similar to E. sullivaniae, but this is significantly out of known range.
Otherwise, I would guess this might be E. album × rotundifolium.
Multiple plants present.
Disturbed area.
Last picture is comparison of leaves from E. rotundifolium, E. scabridum, and E. pubescens.
Escaped, I guess.
Cleared area by roadside. Close to some lake homes, but on undeveloped lot. No sign of any landscaping or planting, but just dry dirt and common weeds. Possibly from discarded wildflowers seed pack?
I guess this could be Lactuca Floridana. I don't have a plant key or open flowers