Should we take lower pay for happiness and subsidize with rentals

[Madison Axmacher]

New to BP and so happy because I have a burning question: does anyone have experience, advice, or even "friend of a friend" stories about taking a lower paying job but but subsidizing income with investments?

Spreadsheets, finance, and calculators are my strong suit. I have little doubt in my Excel plan for rental properties and cash flow. But life doesn't follow a spreadsheet, and my knowledge falls short when it comes to anything that can't go into a calculator (experience is golden and you just can't get that from any number of books).

My spouse and I are very grateful for what we have -- we have enough disposable income to put 20% on a new rental every year if we wanted to (that would be too fast for our comfort, but theoretically). But our incomes have a pricetag -- we both work in industries that rank very poorly on any list I've ever seen about satisfaction, happiness, stress, mobility-- and we are feeling that punch in the gut every day.

We are both considering new careers with lower pay but only after subsidizing our current livelihood with rental income and much more (I'm talking serious calculations regarding current and foreseeable future expenses, going beyond our current disposable income rate so that we can continue to grow, risk calculations such as vacancies and emergency expenses, etc). 

I see no downside other than the hard work it would take to actually get there. And still keeping some sort of full-time employment rather than going all-in rental mode would mean that we still get employer-funded health insurance, possibly 401k matches, some income stability, and having a W2 that shows a solid 9-to-5 makes the mortgage companies happier so that we can keep growing.

It's weird because most people dream of hitting the lottery, and living a millionaire high-roller life but this idea of mine strangely feels like a hidden gem of a true American Dream.

I just had to bring this into this discussion forum because (God love them) I think I've truly outgrown the mom-and-pop advice from the people I know who have never strayed from average nor have they ever tried.

Any thoughts or advice?