I can't really give more specific advice with the information you've provided, but spending your retirement savings and risking your family's financial safety in order to get a nicer job seems unnecessary. You can probably engineer a solution without those risks.
I'm sure you are aware of this, but "not having time" is a relative notion.
Good luck to you, and I hope that you will reach a resolution soon.
Case in point, I'm actually in a somewhat similar situation, and am aggressively looking for an out. After returning to school to finish a degree I was hoping to take a different tack in my career. I really wanted to work on scientific applications with something more in mind than just the bottom line. I accepted a position that offered mostly remote work. They already have an established remote workforce, and it appeared to be a true meritocracy, with little management overhead or fixed structure, and lots of very bright talented people working on interesting projects. I had several interviews, including a day long in-person interview. I turned down three other very solid offers to take this job.
Fast forward a few months and the picture they painted could not be further from reality. The people in the office don't have phones, so talking to them directly always involves jumping through hoops and can take a long time to set up. People are often unwilling to talk at all and prefer to hold terse conversations over IM. Lack of management structure translates to lack of communication and support from above. Some things about the job were grossly misrepresented and there was one major outright lie that would have been a deal-breaker from the start if I'd known about it.
But the job looked perfect! I looked like a great fit to them! This is a career, don't count on a quick fix or finding nirvana in a day, or six months. A friend of mine used to say, life is the process of finding the things that don't work. If you put yourself 100% on the line hoping for a big payoff, you are more than likely not going to be happy with the result. Just look at how many startup founders on here have failed over and over before making it, and many never do. I see no reason to over-extend yourself like that for the sake of a salaried position, at least not without some really clear goal at the outset.
There is no objective measure of great culture or interesting work. I mean, what is "great culture" to you may not be the same to me. For me, I would rather work in an environment where there is a good measure of self-motivated individuals (who get shit done) with a good balance of thinking towards the future (don't experiment too much with a bunch of hipster frameworks that generate a lot of technical debt). And. I like a place that has a great work life balance. On the other hand, there are people who think that great culture means being able to write code in any language, like to work 100 hours a week and who think free food = great culture. Now, I have no problem with that attitude. It is just not my thing.
> , interesting work,
Interesting work: This is a hard problem. Again, this is dependent on you. If you are fresh out of school, everything may seem interesting to you. On the other hand, maybe you have worked on specific frameworks for a while (say building CRUD apps for a BigCo) and now feel like interesting is working on iOS stuff. Maybe you want to be a full stack engineer. Maybe you want to specialize?
> is making money
Be wary, if you are at all looking at a startup. Very few of them are profitable. Most will quote numbers about funding, IPOs etc. It makes it hard to understand what 40 million in funding actually means. Does it mean that the startup is going to succeed? What does a 100 billion valuation mean? Does it mean the company is making money?
> remote friendly.
I think every place in theory is remote friendly for the right candidates. As to whether their culture has ways of workings that make it productive for remote candidates, that is a different issue. If you are a person who is so amazing that you can do your own stuff without face time, almost every tech company will be okay with you being remote. On the other hand, if you are a person who needs to work in a team and work collaboratively, there has to be a culture where the idea that the other person may not be geographically in the same place as you is firmly fixed. E.g. there are small startups in SF where people all come into work at 11 AM and leave at 11 PM. It is a system that works well for them because they all work in sync, talk to each other in person if something needs to be resolved. I like to come to work insanely early, get stuff done, go out and switch off. Some times, I like to get quite time and work from home because I can get a tremendous amount of work done without having to deal with meetings. Again, I wouldn't fit well in the environment that I just listed.
I think we hit all of your points (although "great culture" is very subjective), and our application process does not hinge on OSS/SO profile/GitHub or anything of the sort.