If you are in the BR era it is probably relatively cheap to get a connection from Victoria to Midland some time in the 1970s or 1980s, analogously to what happened to Lincoln.
What Beeching proposed in the Trunk Routes report was focusing all trans-Pennine traffic on the Calder Valley and Woodhead routes while leaving the Hope Valley, Huddersfield, and Peak Forest lines to purely local service (which in Beeching's eyes meant inevitable closure). Passenger service was envisaged to largely be focused on the Calder Valley route, leaving Woodhead for slow heavy freight. It is notable that the "post-war modernisation of the route, providing electric traction" was considered a positive for Woodhead, and there is a suggestion that "the trans-Pennine electrified system" could be extended over the CLC lines to Liverpool.
I believe that Barnsley, now served by services on the line, is a significant destination for the area, for employment, students, etc, along with some useful new stations along the way and the Meadowhall shopping centre, and overall there is far more value provided by running this way. The direct line from Penistone to Sheffield along the hillside didn't run through very much.
The area near the junction of the Victoria and Midland approach tracks junction was being ripped apart in the late 1960s and early 1970s.
The Major Trunk Routes report gave the following reasons for choosing Woodhead over the Hope Valley or Peak Forest lines:
It's also worth noting that at the time more freight went over Woodhead (170,000 tons per week) than over Hope Valley and Peak Forest combined (130,000 tons per week). The report also states that "the majority of the future trains [over Woodhead] are expected to be in the heavy freight class, running at an average speed of 35 mph", whereas intercity passenger service is explicitly mentioned for the Calder Valley route, so it seems like the plan was to concentrate trans-Pennine passenger traffic over the Calder Valley line, which would make the issue of Sheffield Victoria moot.
The choice, had social railway requirements not intervened, would have been between paying for that modification or keeping the Hope Valley line open in perpetuity.
Can you elaborate on this statement?
Well as you mentioned in your previous post, you suggest that they may have wished to concentrate transpennine passenger traffic onto the Calder Valley line, although that seems a bit far out of the way for Sheffield.
Considering the report was of the opinion that the railways should focus on providing passenger service "over intermediate and long distances, while leaving shorter distances and cross country journeys to coaches and the private car", it does not seem implausible that Beeching et al were not especially interested in serving the Manchester-Sheffield market.
I only went through after it closed, which was a shame, but at least I once went through behind 76006 on the way to Rotherwood, fun times!