>fondly remember a game I played as a kid
>afraid of replaying it and finding out it's not as good or tainting the memories it with my cynical adult mind

Does it ever get easier?

I've been drawing almost every day for the last ~5 years and while my skill ceiling and understanding have increased a ton, drawing anything is still a struggle and feels like crawling uphill, I can't just sit down and draw something from imagination in my style and make it look good

I see other artists making immense strides in style and drawing from imagination in a couple of years but drawing anything for me still involves collecting a ton of references and touching stuff up for hours for multiple days in a row and a good result always feels like lucky experimentation rather than an intentional and calculated decision on my end