Years go by and eventually Grandpa gets tired of fixing porches, nailing gutters and steam cleaning carpets that 'have a couple more years in them. 

I am of the opinion that cash flow underwriting comes second, after first nailing the long term deal fundamentals, how strong is the equity upside and market generally speaking. 

Investment Info:

Single-family residence buy & hold investment.

Purchase price: $86,000

Cash invested: $2,500

After being done with Rich Dad, Poor Dad, several podcasts (including bigger pockets)...

., Joey was using a nail gun on the kitchen subfloor.

You hit right on the nail.

@Ashish Acharya: You hit the nail on its head !!

My 2 cents: You're young, you could get a real estate or real estate adjacent 9-5 so you can get paid to to learn more about real estate while learning and building the side hustle outside of business hours.Seems like you live in a major US market so that's a plus, you could get a tenant services coordinator job in commercial real estate making $40-60k (not sure if that's more or less than what you are making now) It's an Entry level role, anyone with a degree and a polished resume and a passion for real estate should have a decent shot at landing a job like this.

There’s huge retal income potential if you nail that balance between improvements that wow tenants and improvements that merely look fancy but don’t justify higher rents.I’d also keep an eye on how your high end plan fits the local demand.

Nail on the head there.

@Christopher MorrisYou hit the nail on the head.The “retire on real estate cash flow” gurus sell the dream of quick retirement from cash flow.Buy two houses a year that each cash flow $1000 a month and retire in 5 years, they preach.Or invest passively in real estate syndications and financial freedom will soon be yours, they promise.What they don’t tell you is:In order to owner enough real estate to generate say $10,000 a month income let’s say, you need at least $2M of capital invested in YES cash flowing real estate.Let’s say one could buy rental real estate that provides a 6% annual cash on cash return.