I almost had it with my talent booking agency (which was bootstrapped over nearly 4 years), and then the money we were making went to a co-founders head and he blew up the company after developing a coke/sex addiction that unhinged his mental health, he couldn't handle the money and the access it gave him and that was at ~50k mrr.... it was like a whole world opened briefly opened up for me before getting crushed.
For me personally I experienced that having an income source not dependent on personal labor has a very strong benefit for being able to focus on execution and setting the company up strategically, it also let me hire devs who I trusted and had a compounding effect on speed of development. I like to think I am a good dev, but I'm not as good as 3-4 good devs, I can't afford that hiring in my current state.
For the homelessness thing in particular, well funded also means well connected, it means you have buy in and backers and vested people going to bat for you. It means I don't have to do all the dev on my own.
That's my current thinking at least.
A follow-up question, is there a reason you want the stab to be well-funded? As opposed to a FOSS, nominal-fee-for-hosting-bootstrap?
From my limited perspective, the worlds' most successful technologies, in terms of (value created) - (costs incurred for each impacted party) tends to follow the FOSS/open model.
Again, limited perspective, but having observed some "well-funded" things from the inside: being well-funded comes with the cost of an incessant demand for outsized and near-term returns.
This demand is, quite frequently, at-odds with net value creation. In fact, it urges your project to become re-distributive: sucking money from bottom-to-top, either directly from the global poor, or indirectly, through government subsidies funded by taxes that are paid by those who need an income to survive (86% of federal revenue comes from individual income tax + payroll taxes, in the US in 2019. 7% from corporations. https://www.taxpolicycenter.org/briefing-book/what-are-sourc...).
The redistribution passes through you, the founder, near the top, which is nice for you because you get to keep some of it, but it doesn't change the net value equation.
All this to say, if your goal is to create real, enduring value, you might be on the right path already, today!