Multiple flows of income - has anyone done this well?

I just closed on my second house that is going on the market for over 500 PITI. My first is barely breaking even for mortgage payments, but we might come back to the area and with tax writeoffs I'm still making a tiny profit especially since I replaced AC/Water heater/Roof within last 5 years. Both should be paid off within 15-20 years and I'm hoping to buy a couple more when the opportunity presents itself.

I have at least a 20% SR that goes into index funds and gets me a few hundred bucks each quarter from dividends+appreciation, hoping to bump that up with pay increases and have it be a consistent 30% once we pay off some of our less desirable (cc) debt. Really looking forward to getting 6 figures in this. Should be far easier to get there once the wife is able to work at the next base we go to.

Lastly, I'll get a pension in 13.5 years or at the very least medical disability payments if I don't make it to 20 in the military.

Should be a comfortable and easy 50k/year at minimum for the wife and I with a paid off house, although I'm shooting for 60+.

/r/financialindependence Thread