Well yea, ridiculous for one, a blessing for the other
The Tool I posted above was created by someone who saw the need for it. And thousands are using it.
And yes you are both absolutely right. In the end you want to sleep.
Every now and then I create routes for groups and then leave booking for hotels to an expert.
For me there are two reasons for the suggestion above.
I like the factor of surprise. I learned that selecting on what i know not always gives me the best experience. Often I am happily surprised by the locations that come out of a more or less random selection. Besides that, I do not think it is a punishment at all to end up on a B&B half way up the hill or on top of a mountain.
So far i hardly ever got the Hotels exactly on the spots where I initially put them. So I stopped putting effort in locating a spot I want to sleep at. Certainly not if the group I travel with is a bit larger.
There is alway reasons why on the specific location/date there is no place for 15 people. And sometimes not even for 4.
I regularly have an acquaintance search and book the Hotels for me.
She is an expert in searching and negotiating. Prices are often better then when I book it myself.
So I split the route in defined segment of 250-350km (Depending on the people it is for) and drop a pin at the split’s.
Currently I make it understandable for her by creating a G-MyMaps overview showing all the relevant information.
I send it to her and she comes back with suggestions. We discuss them, adjust where needed and I change the route based on the Hotels we selected.
It’s just a suggestion.
I am not a programmer so I can not classify the work needed to achieve something like it.