Actually, there is another way.
1. Talk with Reuven and obtain "Get Junior"
2. Go to Cleaver and get "Gangs of Novigrad" going
3. No need to take the Cleaver minions into either location. Just talk with them, but tell them to stay put for now.
4. In the arena, you can go in under cover or as a witcher (or with the Cleaver minions). The minions will attack anyway, but it's THEIR decision, so you're still in the clean.
5. In the casino, if you go in alone to play some more Gwent and then tell them after your assault on the place that you did it all by yourself, the minions will be in a funny mix of awe and surprise and they won't mind it at all.
6. Go to Cleaver and tell him what you did.
- If you went in with the minions, it's a small sum of gold and a happy Cleaver
- If you went into only one location with the minions, it's half the sum of gold and still a mostly happy Cleaver
- If you went solo into both locations, Cleaver knows about it already, gives you no gold and is still a quite happy Cleaver (he saved some coins, but the job was done, so hurray for him)
7. Go to see Roche and continue with Get Junior
8. If you didn't go into either location with the minions, you are now free to sneak into the Junior compound in Oxenfurt via the backdoor, which makes the fight in its outdoor areas quite a bit easier.
No failed quest that way.
I do not care at all about Red Xs on single objectives, so I don't know how many Red Xs this results in.
Now, failing "like 5 missions" otherwise means probably a choice of Eye for an Eye, Redania's Most Wanted, Now or Never, A Matter of Life of Death, Last Wish, Following the Thread?
Last Wish and Following the Thread involve NPCs who must shift their location for Ugly Baby. It's true, there is no explicit warning. You were only told by Yennefer to hurry and that she wouldn't stay for long
The other ones you were warned about when you sailed to the Isle of Mists.