Generating Date and Random times within parameters

So far I have something like that.

So for every 16€ in column "I" a new row is generated. And if there is more than 4 rows for each date in column M, every fifth row generated includes one day eariler. 

I have achieved that with this 

List.Dates([Dat storitve]+#duration(0,23,0,0),[Custom],#duration(0,-6,0,0))

If you have a bteer and more reliable way I would be happy to fix that

But even this is not optimal. Since as you can see for 6/29/2023 there are two incovies (one for 240 and other for 320) so there is more than 4 occurences for 6/28/2023 and 6/27/2023.

Ideally this would look like this

In yellow manual corrections. So no more than 4 occurences on any given day even if 2 invoces overlap.

Is this too complicated?

Once that would be achived then for each row I would require in column date to be generated between 8.am and 6.pm. But hoursthat refer to the same day have in column.8 need to be at least two hours apart.

Does this make sense at all?

Background behind this is that incovies instead of every day are issued lets say once a month per person. So travel orders are to be automatically and randomly generated for each invoice but need to be realistic so that I do not have two travel orders overalping on the same day that is the main point.

Thank you in advance and best regards