2. "I went to school for graphic design and then transitioned..." In response to In response to 0
into web development. Before I got my first web developer role I was a project manager so that gave me an idea of how things worked. You should definitely do some research and see what type of development you want to do because there are a lot of languages and some are going to make you better money than others.
I haven't really faced many obstacles aside from getting to a job and becoming frustrated when the learning stopped. That's when I usually jumped ship and found something where I could grow (and make more money too). I did that a few times until I found a place that is both challenging and financially rewarding and offers remote work. I would suggest it. I definitely consider it a good choice.