Ask a hundred riders for their views and you will get a hundred different answers .
There is no right or wrong .
Your original question Andrew was so broad that it wasn't really a question ,it was more a statement of your own philosophy .
We all have our own comfort levels when it comes to reliance on technology and there is nothing really adventurous about riding roads and trails that someone else has made anyway.
There may be an element of difficulty and a sense of achievement at the end of it all but IMHO ,not an adventure .
Planning is another aspect and some people take it to extremes .I rarely plan anything ,I just have a general goal or direction and set off .The world is a complete missmash of possibilities that it would be a shame to miss anything interesting by adherence to "A PLAN ".
It's nice to have a minimum of good quality kit and I like good quality stuff for a fair price [ hence I don't buy much Touratwat equipment ].Both in travel and at work I find that quality counts ,but do I really need titanium knives and forks ?- no I don't -and a $40 aluminum jerry can when a $10 steel one will do ?- again no ,you get the picture .
I might buy a GPS one day but it won't have satellite radio ,intercomms ,blue tooth and a tea maker built into it .
For some people ,only what they perceive as the every best will do .That's how Touratwat make their money .
Some traveller's lives are so regulated in their daily work routine ,that they cannot exist beyond the straightjacket and simply have to plan their trips to the n'th degree. That's fine too ,but it's not my way .
Sometimes old technology makes sense , for instance ,waxed cotton jackets and leather boots have been around forever and still work in the modern world .I have two modern textile jackets ,one was incredibly expensive [ BMW] and performs dismally ,the other [ Belstaff] was a quarter of the price and is great .But I could just as easily take my old Barbour on a trip .
Old technology was designed in a less complicated world and needs less complicated fixes when it goes wrong .So do we need to insulate ourselves with technology ?
No, we don't --but it does give some people the illusion of security [against the wild and woolly world - "out there"].
So I have to say that I agree with you ,some riders do obsess about equipment and planning and miss the big picture .