Interesting 100k Challenge

[Christian Lincoln]

I don't know why this fascinates me so much (and I recently pitched a reality tv producer about it - with a charity bent to it) but the idea of turning a certain sum into a much larger sum in a time frame captivates me in an unhealthy way. (leans more towards the aesthetics of leverage and efficiency and freedom than greed i think). Probably because I don't have a family now, no kids, and a few years away from turning 50, I don't feel the need to be as "conservative" with my investment strategy (diligent and aggressive, and smart: yes) as I might normally. Feel the need to make up for lost time maybe. But I'd like to hear people weigh in on turning 100k into 100k of passive yearly income in say, to be fair, five years. Not too over-the-top in aspiration. The goal being enough net income to write, read and sail without worrying about bills. That's it. I don't need anything else like toys - but only to be relieved of overhead, bills, and normal stress. 100k annual net does that fine.

assumptions:

Added variables:

mediocre credit

I'm a very good all-around carpenter, but want half my day for my creative life.

highly creative: would rather put that energy into other areas of life that renovating and design but willing to mix rentals with flips for a few more years.

have a couple nice houses that only break even now. no cash flow.

willing to invest anywhere in US or Europe. Love California (too late there i think), love Spain (still good there i think). Live in NY. Missed the train in NYC, too rich for my blood, but upstate still deals. Florida?

thank you kindly for any an all who weigh on this "What would you do?" question.

-Chris