Especially looking to hear from anyone that has successfully attained this sort of goal and able to share their input.

Depending on your income, however, the 0% capital gains tax is still possible to attain if the sum of your joint income and your son's income lands in the 15% bracket or lower.You mentioned you're teetering between the 15% and 25% bracket in 2017 and your income will be significantly lower in 2018.

The passive income is attainable, the deals are just harder to find and of course harder to make sense with rates.

Thanks for the story, you made it sound attainable.

There is an infinite amount of ways to get and attain deals.

Working in path-of-progress, sweat-heart terms from developers attaining sub-market rates, superior inventory, leading to superior tenancy and done correctly, superior returns. 

Look up value add repairs to see what would be attainable while building ARV in a short timeline.

i will be doing more research to see if this plan is actually something attainable or if i'm missing a piece of the process.

Ideally with a positive cash flow , but overall certainly want to invest in single family homes that i can keep for the long haul to be able to slowly attain financial freedom 

I believe that (most) of your goals are attainable, but you would be wise to seek out assistance and receive personalized advice rather than what tidbits can be shared on these forums.