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Have you completed the Ruin sidequest that you can pick up from Captain Bernard? Once you get to the Sasau area the enemies are higher level, that's where you'll fight robber knights in plate armor and the like. Tons of money to be made that way too, although I imagine you're already rich if you're level 20
Sound like you need to go HardCore mode. The fights are much harder, especially against opponents wearing plate. At a certain point, normal mode ceases to be fun as the fights are just way too easy.
The bandits around Skalitz are challenging, and I often run into gangs of well armored bastards on the road NW of Sasau. The road encounters are random, which is why they're fun as you never know what to expect.
Scout will just let you avoid encounters, it does not really affect the odds of having one by itself.
In my experience, Fast travel tends to have far fewer encounters than just riding around, and it also depends on how far you travel, where to, and what path is chosen for you. You may already know that there are designated ambush spots all over the map, but Fast Travel paths only go by a paltry few of these. For example, there are at least four ambush sites on the roads to Vranik, but the Fast Travel routes only take you past maybe two of them.
If you want to encounter more ambushes in any stage of the game, avoid fast travel and just ride to your destination, go the scenic route, take some paths you normally wouldn't. For some challenging ambush encounters, take the road east out of Pribyslavitz or southwest to the Skalitz mines: you can get ambushed at three places right there.
If you're really into challenges, I would also suggest going through Hard Core mode; as mentioned above, the opponents are tougher and the game play is less forgiving. Load up on Savior Schnapps and know your save camps.
Hope this helps, and enjoy.
Best thing to do is ignore fast travel and travel around yourself. If you know where they are it will be faster.
It doesn't matter what quests you have done or not. You can encounter any of them from waking up in Rattay.
If you want I could list you some good encounter spots.