This is a hard question to answer because there are still people that make a living doing everything under the sun.

Are you asking because you are concerned about the field dying? This would be a viable question, so I will assume this is your actual question.

I would get involved today, not tomorrow, today. Contact a web development business in your area, or online and talk with someone. Ask them about what kind of work they are doing. Contact a few different types of web businesses. The smaller/medium sized ones are more likely to give you the time of day instead of just a secretary that will give you someone's voicemail.

My son is 17 and got an internship last year with a local company doing web design. (minor dev work) And now he contracts with them from time to time. The business owner would hire him right now full time, but agrees with me that he really needs some life/education under his belt first.

Every field out there _needs_ hard workers. People that will show up, have a good attitude and learn, learn, learn. Being a rock start is far less important. This is odd to hear when you are on the other side of this equation, but trust me, people hiring these days will hire for character and work ethic over perfect job skills, you just need to be able to get your foot in the door.

Last, find the kind of "web dev" you want to actually do. You couldn't make me do anything else right now in life, I have to do web dev, it's not a choice I could walk away from, it's what I like doing and I have no interest in other work for the time being.

You asked "risk more time and money", everything is a risk in life. There's very few absolutes. The question is are you willing to make it work? Web dev isn't like driving a truck or being a nurse where they teach you almost everything you need to know to do your job. With web development you have to keep learning and be ok with this. And you start off not knowing enough to really do the job perfectly. I am mostly self taught, and I had to go through years of re-educating myself out of bad habits, and deciding to chose industry standards and chosing the hard, but right way, to do things.

It's always paid off for me, but then I like learning, I like seeing fascinating solutions, I like puzzles and problem solving. I'd do web dev as a hobby if I didn't do it for work.

My last suggestion is to get started how I did, build something you actually want. And keep doing this over and over. I never wasted any time doing this. I made everything from my own text-to-speech tool (silly and half baked) to a full CMS. When in school I made multiple websites, games, apps, multiple portfolios, (trust me, a lot of this stuff was total crap, but I really learned a lot). Everyone else in my class did the minimum to get by. I've learned databases, server management, a few different version control systems, multiple languages, animation, design theory, etc... It's all been interesting, fun, often stressful, often exciting, but always useful.

In the end, if you don't find work, either keep looking until you do, and keep up your skills (always, always be working on something) and eventually you will find something. It's just a numbers game. Or find satisfaction in whatever job you find yourself in outside of web development, it's always an option for some people.

Cheers!