Hey @Aaron K. thanks for the questions.
Yes I mean annual numbers. My projected expenses after leaving my job will be in the $30,000 a year range until I return to gainful employment. I am hoping that the properties I lock in prior to quitting can bring in that much so I do not dip in to savings while traveling around areas with low cost of living (SE Asia, S America and our off grid RV in the states/Mexico).
After purchasing my second property (allocating $130k) I will have a remaining savings of $200,000 which I prefer to not dip in to. While living the nomadic unemployed life I would likely invest this in other value add rentals.
If these numbers don't come to fruition then I can (1) dip in to savings or much more likely (2) do freelance software engineer work remote and part time.
I would consider the whole endeavor successful if I can:
1- Generate 30k a year in cash flow from existing rentals prior to quitting
2- Live off of just that cash flow for 3 years.
3- Over the course of the three years invest my remaining $200,000 in to more solid cash flow rentals
4- Return to work with a larger RE portfolio then when I left and no more angst about spending large portions of time in an office since I had just spent three years on the road.
You are right that a $500k property or multiple properties adding up to $500k would generally not cash flow $20k a year w/ 20% down in those markets from current turn key MLS listings I am seeing. I am hoping that I can get closer to those numbers by hunting for deals and doing most if not all renovation work myself.