@Reent, I totally understand the lack of appeal when you put it like that, don't worry
FYI, You can upscale WM1, if you go to Stalwart for the first time at level 9. As a matter of fact, I never played WM1, WM2 or even Act3/4 without the upscale, so I don't know exactly what it changes. My only point of reference is monsters you meet in both Od Nua and early Act3 (I'm faaaar from done with the game, taking my sweet time ), namely Adragans. Those are terrifying for my party in Elmshore, and absolutely not a problem at all in Od Nua or those Engwithan ruins near Dyrford.
It's certain that Upscaling upgrades all defenses by around 15 points, pushing most POTD monsters into Dragon domain, but I suspect upscaling also boosts the base attributes (Int and Dex in particular) which vastly increases the range, duration and speed of their abilities. A single Moonwell by an upscaled Adragan for instance will heal the entire screen for considerable amounts each tick, and their Returning Storm will hit your backline without fail. They will dominate faster than you can suppress your petrified teammates, and generally speaking, it takes a hell of a lot of tactics to just deal with them even in a full party. I don't recall having so much trouble with them, 5 levels ago, when I was still trying to reach level 9 to unlock upscaled WM1.
Whether that's all because of increased defenses and my party's inability to oneshot them (along with its strange composition, 5 melee and no casters), or whether they do have increased base attributes allowing them to pull off dirty new tricks thanks to increased range, speed, power and duration, I'm not sure and I can't say.
Regardless I have faith that your general strategy is sound and skews the numbers game hugely in your favor, so much so that even with all this your chanter would probably be successful (eventually), just like you managed to deal with increasingly harder odds in WM2.
Upscaled WM1 was a considerable challenge for me with a full group of level 9s. I guess I might attempt it without the high level toggle with the same group later on this year; maybe I can get closer to the truth about upscaling that way.