I was in the same boat as you Dave. I hadn’t used Windows since NT, so luckily missed the Vista and Windows 7 debacles
I really wasn’t sure what to expect when I purchased the Surface Pro last year, but I found it wasn’t hard at all to learn the basics and I purchased a couple of books to learn more in depth. Not unlike my switch to Mac where I still have books on MacOS Tiger and Leopard around the house. They make for good references if you get stuck.
I was really hesitant to make the switch, but found it was far easier to make the switch than I thought It was going to be. The hardest part was breaking out of the mindset of having had nothing but Macs for all those years.
I am not at all an artist, so I don’t know much about drawing apps or their equivalents. I do like the adult coloring books Apps for unwinding and find that is still something I prefer to do on my iPad. Not because the pencil is a better tool, but because the apps are better than the Windows equivalent. I know nothing about Pixelmator, so I don’t know what the equivalent would be.
I do spend very little time with my iPP since I purchased the Surface Pro. It is mostly the coloring and checking news and email before bed and when I wake up. A bedside table device for the most past these days.
I am not trying to steer you wrong and I realize the Surface devices aren’t for everyone. But it sounds like you are not fully satisfied with what the iPP brings to the table and are looking for a device that will fill the role of what you use your iPP for as well as what you might use a MacBook Air for. A Surface Pro might be the fit .