Tales wasnt actually part of the main LucasArts series, so if LucasArts continued it probably wouldnt pick up from Tales. Telltale hasnt said anything about a season 2 of Tales.
This is false. Tales IS a part of the main series, as you'll notice the big Lucas Arts logo in the beginning, and the fact that Lucas Arts licensed it to TTG so the series could continue. Tales is MI5.
Both TTG and LA have spoken on the issue.