Although I've only been painting for a relatively short period of time (some six years on and off), I have found a lot of pleasure in creating portraits, mainly of people I have come to know. I first started with rough sketches and developed well enough to try my hand in painting with acrylics.
It was a hard learning curve and acrylics tend to create their own unique problems, what with drying very fast before blending has begun, but also darkening colour as each pass dries making it hard to match colours at a later stage. This is very frustrating, and often requires repainting larger areas with fresh paint.
So I tried a move from Portraiture to Landscapes, hoping the process would become easier. Alas it was not, so I then began watching a lot of online tutorials. Very helpful. I am also in the process of moving over to oils (and another steep learning curve) with its own problems.
Don't you just love learning!