To me, this seems orthogonal to whether you have technical assistance in your planning or not.

I'm currently traveling through Argentina. I don't necessarily know each day where I will stop and certainly don't plan this a week in advance. I sometimes have a few alternatives for a day and determine based on how the day goes.

When I have a gap between towns of 220 kilometers, I typically can make it across in two or three days but occasionally need four days. It all often varies on whether the road is paved or gravel, what the wind does and how many hills are along the way.

If I look online I can get additional information including recent trip reports, weather forecasts for the wind/rain and elevation profiles - to better set my expectations. With those expectations, I will also know whether there is likely some surface water to filter or whether I need to carry water for all the days.

Without this information, I am going to leave town with a heavier load to handle the worst cases e.g. gravel road + extremely strong Patagonian headwinds (*) + some steep hills + no ground water = more days on the road and more food and water to carry.

With extra information, I may leave town with a lighter load because I have different expectations, e.g. entirely paved + water in the rivers + relatively flat with weather forecasts calling for lighter winds + a little store along the way = likely fewer days on the road, better supply and thus less extra food and water to carry.

In neither case will I necessarily know where exactly where I will stop in this gap (although if I know in advance there are fences along a lot of the route but a place people have camped further along - I might push it a bit to that camping spot) - just that technology has better set my expectations. In both cases, I still need to account for some unforeseen events, e.g. road construction or store is closed or faulty forecasts or mechanical problems, so still keep some safety buffers.

(*) As an example, across one of these recent gaps, the weather forecasts indicated a few afternoons with 60-100 km/h wind gusts. I took some extra rest days for the storm to pass and was happier to have had this information than to have set off a few days earlier.

Bill in the video was typical of thousands of bike tourers in Scotland in the forties, fifties and early sixties. It was common at that time for people to leave work on a Friday evening and set off for the Highlands and Borders of Scotland using Youth Hostels and cooking at the side of the road with their Primus stoves. It was a golden period of cycling in that there were not too many cars on the road and every small town and village had its cycling club.....many marriages were made between club members. I used to spend hours listening to an old cyclist in his nineties who remembered wrapping himself in his cycling cape and sleeping in a hedge if he failed to reach the Youth Hostel in time. Many of these could really put in the miles and I'm still friends with some who were part of the "300,000 mile club".

I enjoyed my Musician's pub crawl , of Ireland, and Scotland 20 years ago, I had my 50th birthday on this day, back then, 97, in Forres Morayshire, Scotland.

Thats not hard. Shouldn't need to stop

Now no one use the old style of touring but yes we can say that combination of old and latest style help to make a new style which is very effective for all of us.

Meh; if you can paddle a straight line, it'll never be more than 350 miles on Superior.

What I find the GPS handiest for is quick planning; I don't remember all the back roads from here to Weatherford, but I can have a complete route with cue sheet in about 3 minutes from OSMand, then pull it up at need to get back on the route if I take a wrong turn or detour around a problem. It also tells me things I might not otherwise know about the roads near the route, like whether the town a sign points out 2-3 miles off the route is just a named chunk of road with a half dozen houses, or actually developed enough to have a gas station.

Eating fried chicken gizzards, a raccoon making off with your cheese, hanging your food from a tree in case of bears, smoking a cigarette at the top of the hill ...