This would make a good movie, or at least a miniseries.

Get rid of debt.
Save for starvation wages, now.
Housing, food and transportation are typically biggest three mnthly costs-find savings there.
Most places above regional crack six figures in the second year, so really just a year at ultra low pay.

Sell the third boat.

Great advice, do most airlines allow 2nd jobs...? As long as it doesn't interfere with rest/flight regs?

As long as it isn’t flying then yes, you can do whatever you want. Lots of guys own their own small business or dabble in something on the side. If you’re really hurting you can drive for Uber/Lyft/any of the food delivery companies to make extra cash while passing the time on reserve but I’ve heard it isn’t much money for the amount of time you put into it. Obviously save if you can and pay down as much debt as possible before making the jump but it really depends on your situation. I was able to do it by just cutting back and using credit cards when times got tight. A large family with a big mortgage and multiple car payments might need more drastic measures (moving, selling cars, having your spouse pick up another job, delivering pizzas, etc...)

Brothels are too hot right now.

In most places it's very easy to get checked out as a substitute teacher for your district. Get into that system and sub a few times (especially at the schools your kids will attend) and get your eyes opened with a true behind the scenes. Pay is not much, but the experience is grounding, and the few districts I've been in only require 2 days a month to stay in the system. You'll meet a lot of people in the community, and some very hardworking (and some not so) teachers trying to do their best.

Plan your finances out to year 2 at the career-destination major. There's always a price of admission to civil aviation, you either save up in advance (what I did), get a part-time job, or adjust the lifestyle accordingly.

Regional pay is a lot better than it used to be, but if you're coming from the real white-collar world something is going to have to give.

If you have skills which you can do on a laptop, you can take it on the road with you (accounting, computer programming). If not, then uber on days off I guess.

The transition to major FO will be easier, most majors will get you to 100K (or significantly more) in one year so you might be able to bridge that gap with credit cards. Most of the better majors pay about 100K first year.

The hardest part is really transition from white-collar to student/CFI/regional FO.

I'd simply pick up as much extra/premium flying as I could 1st year if you can stand being away longer. Most of it is at 150 or even 200% of course, which even at the regionals, will make more than most side jobs outside flying.

My strategy has been to live poor my whole adult life so having no time or money will feel like an effortless transition. Feel free to message me if you need advice on how to not have a lot of money