Looks clean as a whistle, Keith; glad it's in your collection. I used to own one, too. I don't believe the tool set is not from its production era. Mine had the standard 4-piece Model 3250 set with the oval graphic on the carton like your smaller one. Maybe yours was sold at the end of the run, because it's the same color. Btw, what is stored in the small carton?
For the benefit of those unfamiliar with the Model 36 it's a "Convertible Special" with limited features - sans headlight, hand grip and pedal pads, snap outer bag rather than zippered, and shorter power cord & furniture guard. The color is tropical island green, and it was manufactured from 1966-68.
This was produced early in the run with the Hoover medallion. In May 1966 the company switched to using the smaller Hoover decal.