*I plan to pay the taxes on the stock, TTL on the vehicle, and closing costs on the house(s) out of my own pocket in order to stretch the $40k the furthest. 

Your logic from another perspective sounds like this: "Banks shouldn't force us to make payments on vehicles, credit cards, mortgages, student loans & SBA loans, because unlike most people, they have unlimited cash due to quantitative easing..."

Going to deep clean the interiors of our vehicles.

im not an expert/professional this is just my 2 cents. but with the amount of debt you owe i would not file for bankruptcy. go get your engineering job back, negotiate the debt you have many places will let you pay less or at least give you a payment plan. find a good tenant and rent the duplex out. as crappy as it is to have those payments it will help you in the long run. and if you can cash flow rent the other side of the duplex and live rent free you should be in the green in no time, unless there is more to this...obviously alot more information is missing. can you sell your vehicle and get something cheaper?

I still only drive made in USA vehicles, just it's not so easy to spout off that everything I have in made in the USA.

Paying for vehicles or gas = ?

Paying off 1999 debt with 1999 dollars just locks your money into a vehicle that produces no income. 

All new windows, electrical, new plumbing & furnace, new heat pump & new garage door and motor.

Keep in mind that there are laws about vehicles and high valued items that will have leins on them. 

For my business, I have vehicles that aren't solely used for the business so we capture those miles in a program called trip log.