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.