[catwind7]

> Is the Web Dev job market in a good enough state

There's a lot of demand for devs across the board (this is my gut feeling from participating in hiring at my current company). This probably varies a lot across teams in a company, across companies in an industry, and across industries.

One strategy I recommend is to narrow down your target employer market so you can get more specific answers. What industries are you interested in? What are some companies you might want to work for? Do they have an engineering team (most likely). Then figure out what roles they have open and do your best to position yourself for those openings once yo u start interviewing.

> that I should risk more time and money?

What kind of self-learning have you already done? Can you give us some information about the courses / tutorials you've been following? Is this something you find yourself enjoying?

More details about your situation would help. For example, if you've mostly been following a coursera course for the last six months that's heavy on the theory side, I might recommend that you spend more time with something more hands on like building a web app to solve a problem you have.