I always encourage students to get comfortable with the shorthand as quickly as possible, though I focus on the skeletal structures. The abbreviations (Me, Et, Pr,…) are less critical.
Using skeletal structures allows you to focus on the important parts of the molecule without getting distracted by every C-H bond in the molecule.
To use your directions analogy, the short-hand is like saying: “Go straight 5 blocks, then take a right,” while using complete structures would be like saying “Go straight 5 blocks while passing Target, Walmart, KMart, Kroger, Winco, the blue tractor, the gas station, the YMCA, the VFA, the left hander’s store, Walgreens, Culvers, McDonalds, and the minimart, then take a right.”
The ‘complete instructions,’ are correct, but they include too much distracting information.

Wonder how many people have problems understanding the various shortcuts and how that might affect the reputation of ochem as incredibly difficult. Essentially the subject teaches several ways to do the same thing that are just different enough to be confusing for most people if taught at the same time.

Perhaps a good analogy would be direction giving. When most people are lost and asking directions from another human, they don’t want an answer like “well you could go this way ’bout a mile, then make a right at the broken down tractor. Or you might take this road for half a mile, then take a left onto Old Hillbilly Lane and follow it for ten minutes. Still there’s also…” We tend to want one way to do things at a time.

As computers overtake paper it might come to pass that the shortcuts won’t be necessary. So my question is could one ignore the shortcuts if they had the time/patience, get comfortable with the material and then come back for the simplified methods later? (Learning just the simple way and coming back for the complete way seems like a bad idea.)

It’s true – drawing structures is a crucial skill set which is often very poorly explained.
Grossman’s first 2 chapters basically cover a lot of the common mistakes that are possible for students in Org 1/ Org 2. Grossman’s rule – which says you should draw out hydrogens at reactive centres, as per your recommendation – should be more widely taught.
https://masterorganicchemistry.com/2011/10/06/grossmans-rule/

Having said that, it’d be nice if organic chemistry courses allocated a few lectures to drawing structures.

A huge number of conventions (the shortcuts you’ve mentioned and others) I’ve seen organic chemistry teachers write up or refer to, without having ever explained them.

The same deal appears in many textbooks – I don’t think ANY are entirely free from this stuff. I remember reading a sentence in Ege, I think it was, or another one of those textbooks for Org 1, about the importance of learning to draw well – but that was it.

I actually searched long and hard for a book that would teach when certain mechanistic conventions were allowable, and when they weren’t. A combination of the stuff scattered through Clayden, and Robert Grossman’s excellent book ‘The Art of Writing Reasinable Organic reaction Mechanisms’ have answered most of my questions.