I'm a digital artist, genuine question what issue do you have the apple pencil and iOS ? I use adobe draw, sketch, comp and photoshop mix and they work fantastically and are powerful apps for what they aim to do. As a digital artist I also have the obligatory Creative Cloud subscription anyway, so I can sync my projects to the creative cloud and then open them, with all layers intact on my workstation and vice versa and work away.
Likewise Sketchbook Pro, Procreate, Brushstroke, ArtRage, Paper, Penultimate and Pixelmator are all excellent in their own right and wotk fantastic with the Apple Pencil. Also for recreating brush strokes and pencil shading, the Apple pencil is amazing.
I had an i7 Surface Pro 2 with Wacom, before they switched to N-Trig and the biggest issue is simply a lack of optimised apps. Sketchbook Pro on Windows has noticeable lag when drawing, compared to the iOS tablet version. It also can not recreate the shading aspect anywhere near as well. Worse still apps like Corel Painter are very laggy and because they still are not updated to HiDpi displays on windows, their menu sytem at 200% (default scaling of Surface) elements of the gui are broken and pixelated inside the app. Switching to 100-125% scaling fixes the broken gui elements of the apps but then menu systems and brush selection tools become extremely small and finicky. What should be effortless drawing time, becomes a concerted effort to utilise.
The Surface is a fantastic tablet hybrid, but simply from a illustrator perspective as soneone who draws every day and works with a stylus 75% of the wirking day, the Ipad with Apple Pencil has far less issues and a much smoother more natural feel.
However if you are looking for the better hybrid device for things outside of drawing, the Surface is a great device and i wouldn't have any problem recommending.