Regarding:

> I really just want catastrophic coverage where I pay ideally $XX/mo, have an $XX,XXX annual out of pocket max & deductible, but that doesn't appear to be an option in my state's healthcare.gov program.

… in most states, the marketplace includes plans with $5k-$10k deductibles and out-of-pocket annual max of about 2x that. For a non-smoker under 40, the premium will probably be $250-$400 (depends on age, area cost of living).

That's the viable version of the plan you described.

There's 2 main reasons that no plans offer something like a $25,000 deductible and $50,000 out-of-pocket max:

1. State insurance commissioners and the ACA require certain minimum coverage. For example, the ACA requires https://www.insurance.wa.gov/what-health-insurance-plans-mus... and Washington State requires https://www.insurance.wa.gov/benefits-health-plans-must-cove.... Some of these require certain paid coverage levels regardless of deductible; for example, the ACA requires most preventative care be covered without out-of-pocket costs.

2. Increasing the deductible and out of pocket max significantly (say, $25k/$50k instead of $6k/$12k) doesn't decrease the insurer's total costs all that much. For plans with $5k+ deductibles and $10k+ limits, the insurer's major cost is six-figure treatments, and the insurer will be responsible for those either way. Just to use hypothetical numbers, raising the plan limits 4x might decrease the premium by 20%. Most of the cost is either item #1 above or really expensive treatments, not care that costs $6k-$25k.

Second, to clarify, I can afford the insurance premiums with operating investment income alone, without touching my principal, I'd just rather not spend half my operating income on monthly insurance premiums that exceed my typical annual total healthcare costs. Frankly, it's frustrating that I even need a prescription at all for my medication. It's for a stable, lifelong, uncurable but minor condition. The medicine does not build tolerance or dependence, has zero recreational use, and is not even a component for any kind of recreational drugs. ~90% of my regular annual healthcare costs is my once-a-year doc visit that my doctor requires in order to renew my $3/mo prescription, but that's besides the point.

Demographic is under 30 nonsmoker, for whatever that info is worth in evaluating this.

I can always delay my departure from my current employer, push come to shove. This will be a resignation, not a layoff / fired type of situation, which I am grateful for. Sounds like that's option 1 for expanding operating income.

It seems like right now you're trying to make the investment income fund everything, but it doesn't need to. Your income from the new consulting company will be lowest when you start, so give yourself 6+ months of cushion that you actually expect to spend. If you go 6-12 months and have spent the transition fund without finding new income/consulting clients, then you can go into the "ramen mode" as needed.

In practice, that doesn't seem like an actual situation: if you go 6-12 months without bringing in at least a few thousand dollars a month in client work, then do something else - don't keep going in ramen mode. That something else might be finding a partner who is good at sales. Either you have a viable consulting business after 6-12 months, or you don't and should do something else :) There's not really a case where the investment income needs to fund all your expenses indefinitely.

Again, thank you for your wisdom! It is greatly appreciated.