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Which situation would the ATC have had his behind on the line for had
something happened? helping guide him into OSH knowing he wasn't
prepared, or refusing to do that and insisting that he turn around and
go back?


As I recall the ATC didn't do either of those. He explained the VFR arrival
procedure to him and told him to remain clear of the Oshkosh Class D
airspace while on his way to Ripon.