Beating a monster/clearing a cave etc. that is at a higher level to yourself via luck or skill is where the "yee hah!" moments lie
A lucky win can be good, it may be a relief and a surprise, but there's no talent on my behalf involved, so nothing for me to pat myself on the back for.
A skillful win, which you worked to gain the necessary stats, worked out the plan and executed it perfectly? Absolutely.
Don't think these 2 can be conflated, though.
Please consider replacing the hard requirements with die rolls for the stat checks in the Contract Missions.
As an ex-player of many mobile games that employ it, I can honestly say that I absoluely detest RNG as a game mechanic.
For me, it's not an achievement to gain something, if it's simply a random occurrence.
It generally only feels good, because you've done the same thing x50 and got frustrated/disappointed with receiving garbage, before it decided to randomly award the item you want/need.
I view it as an achievement to work towards something, build our stats high enough & devise a strategy to conquer it, then beat it.
I earned that. That's satisfying. It's within my control. Not a random die roll gave it to me.
It's really not that big of a deal, here, anyway. The analogy you gave is for something extremely difficult. This is really not.
Completing a couple of objectives in the 1st contract only requires the purchase of a hat and trousers, which you can afford from the start.
You can run the 1st contract a few times, just with the 2 stealth thefts & this will give you enough to buy equipment and gain a promotion.
When you have earned enough for better equipment, you can then earn more from the mission, by completing more of the objectives due to the increased stats.
n.b. You also increase your stats by completing Side Missions, for the girls.
Isabel's grant Charisma.
Gracie's grant Intelligence.
Luna's grant Agility.
I thik it's a total of x3 points for each stat, from the girls.