>If you had the time and money, would you do a bootcamp, or a degree, or work on your own?

Unless I knew for certain that I couldn’t do solo work, or knew for certain that I couldn’t muster the discipline, I would say “work on your own” in the beginning.

If I am to take your harmonious financial arrangement at face value, which you reaffirm in another comment, understand that your situation is probably very enviable to many. Make the most of it.

You didn’t specify but I assume you expect this situation to hold for at least a year, maybe two or three years? That’s great. And you already dabbled in ML, and you “really like it”? Well, its the remote option, but this is what I would do :

1. I would brainstorm a project about applying ML to law, or my field of law[0]. This is not completely unheard of, as I’m sure you’re aware.

2. If I come up with some holy grail ideas, I would put them aside for later. I would then try to find something to start with that is very simple, maybe something that would have helped me day-to-day in my previous lawyer life. Maybe something much smaller that would be a necessary but not sufficient item for one of the holy grail ideas, or like I said some small but obvious value added day-to-day lawyer stuff.

3. After I decided on the project, I would apply the Amazon way of working backwards,
a. Create the press release: Describe in simple terms what you’re going to build
b. 20 most frequent questions: Answer in clear, simple terms (& iterate until it is very clear what you’re going to build)
c. UX Document: How are my users going to interact with this
d. Keep the above simple, don’t overdo it.

4. So you came up with your first project, now you have to skill up. Since you dabbled in ML maybe you are already familiar with the ML learning angles people recommend on this site (fast.ai, Coursera etc). I would research and make a decision which ones to start with first (maybe you’ve already completed some) and focus on completing them together with all the relevant exercises etc. In parallel, I would be on the lookout about what I need to learn for the project and continuously apply what I learn to the project.

5. Out of necessity, you are probably going to need to dabble in integrating frontend web and mobile stuff. Research and decide on learning path based on what concrete things you actually need in your project.

6. Once you feel you know enough to build the shittiest and dumbest version of your idea build the shittiest and dumbest version of your idea before continuing a new online course in your studying plan.

7. Put your code on the web when you have the shittiest and dumbest version of your idea working and keeping updating it. I would upload two separate things as projects
a. the software/product that the end user will use that has everything in it.
b. The ML component as a separate project. Don’t let the frontend stuff detract from the ML stuff. Imagine someone with better web and mobile skills wanted to use your ML-law work to make something more polished. They could use this.

8. Now you have a portfolio, don’t you? You could go on building the next item on the road to a holy grail, or you could continue iterating on this as you learn.

9. Meanwhile, you could start applying with your portfolio for remote work at AI tech companies targeting law or NLP areas (more general overlapping domains) , or law firms that are scared of tech who don’t want to be the nokia or blackberry of law in the future (this is probably the unlikelier of the two, since this tech would disrupt billable hours). In the former, you would be the “domain” guy for the tech, in the latter you could be the “tech” guy for the domain. Your skills and background will be unique.

10. Alternatively, or in parallel, start selling what you built. Cause looked at it another way, this is identical to have received seed funding for 1-3 years to start a company.

Sure when you start working with others you may soon feel you’ve missed out on some fundamentals, but this is what I would do in terms of opportunity cost. By the end, you will have a unique background and you will be working in a niche area suited to your background, your weaknesses will matter less. After this, if I still felt iffy and it still didn't matter if I got a job or not, then I would consider a online degree through a US institution, but if its a very good program.

Anyway you asked me what I would do, obviously might not be the best advise (disclaimer).

[0] assuming doing anything related to law or your field of law doesn’t instantly fill you with dread or actively demotivate you in whatever you’re doing. If I hated law, the general outline would still be the same. Coming up with a project idea that kept me motivated and that I thought would be of use to others might take a little more time to find. I wouldn’t be able to use my law background for applying for work for maximum effect, so there would be no binding narrative between my previous lawyer life and what I’m doing now, that might make it more difficult to sell myself to potential employers. But with a portfolio that would matter less.