Wow this has gotten lively today! The bit I put in brackets as a side note about Luke having not flown an X-Wing has been focused on.

Luke flying his skyhopper through the strong winds and gravity of Tatooine with canyon walls as points of refrence would leave him ill equiped to fly a Starfighter in 3Dimensional space with no point of refrence. However his experiences in Beggar's canyon would be ideal for the trench run if he somehow managed to get his X-Wing to the trench.

But my original main point hasn't been addresed...

Ryan McAvoy said:

And in the original 1977 film where Luke is leading the trench run with two much more experienced pilots as his wing men is totally fine? Luke leads the trench run because he is the hero that we are all rooting for. It makes no sense logically but it feels so right.

Why is Luke automaticaly leading Wedge and Biggs, who are we assume more experienced starpilots. Even if we believe they've been in the rebellion for just a day longer than Luke, it's still longer than the hour Luke's been there.