I personally love the contract missions, at least the first couple of times I go through a mission, when there's still new stuff to discover. But re-doing the missions when grinding for money is a bit of a chore
Maybe if the missions had some kind of randomness it would be more fun to re-play them. Though I have no idea what that would actually look like. And honestly, it's not enough of a deal breaker that I'd want development time wasted on improving it.
Like Whichone (said above), I liked gaining more valuable equipment.
First time on the contract? I may get "rare" rank equipment, but the best reward is "epic" level equipment.
So the rewards dangling (I guess like a carrot, heh
) prompted me every time to do better in my future contracts by either grind earlier less challenging contracts (which I 100% before), or doing free-roam events which also give premanent stats boost.
There is a bit of grind for money, but I think it's pretty mild with this game (I've played/heard other games which are waaaaay worse than DeLuca), and I do think the main story will have events in the future where MC will gain money every now and then (like the Beach prison event).
I've actually grinded to pile up some extra money even after I finished all the content in the update. My mindset to it was "stockpile some money now, and less hassle for it later."
There's also the case of equipment in upper tier contracts possibly being more expensive than the D-contracts.
But that might not be what others prefer.
With randomness, while it's certainly an interesting idea, I'm not sure how that would actually work.
MC's stats being used for combat situations, stealth situations and others is something that is the backbone of the contracts, and I don't think it would work if that is taken away. Some might be saying "perhaps these can be done with a roll of a dice" but nah.......really not a fan of those RNG gameplay types, and I think it would lead to more frustration than others.
Another possible way would be to randomize the contract's map, by each contract having 3 or 4 maps with one being randomly generated in each playthrough (but still having same story), but I think this is a waste of time (value obtained from the randomness feels far too small compared to cost and time, resources likely to be spent on them. Besides, with new maps, I would have wanted new stories, not using the same ones, but that's not the point of the contracts, since they are to be repeated in order to 100% them, and not one-shot in a single try).
Repetitiveness is one of the very small inconveniences I guess of the contracts' crux:
"repeat until you master it and get the best equipment and those special renders"
Having said that, when I grind for money, I just do the whole fast ctrl skip through it all (considering I know the directions to go off by heart after first couple of tries, they get done really quickly).