If you are planning on making a living or becoming financially independent, it will come much faster owning the homes.

I currently own one unit in Florida and used to be a mortgage broker before I moved to California to work in the entertainment business..For the last decade I've given myself various financial "challenges" to help keep me focused.

All the financial doc's were provided and the numbers simply did not work..

This post is kind of an introduction and a search for advice.I have recently discovered real estate on my search for financial literacy.

I plan on doing this with my long term friends they are all financially stable and have jobs and the income to support the move.

Goal is to create enough income for financial freedom.

One of the companies we really like is Roofstock, as they appear to do a lot of the legwork for you (finding, what appears to be, decent rental units, along with calculating all of the financial information).My question is, has anyone bought through Roofstock before and looked back to see how accurate the Roofstock calculations were (cash-on-cash, turnover repair costs, cap rate, etc)? 

@Daniel Dietz,Ignoring the internet deduction issue, would make sense financially for you ? 

This is very doable for me given my current financial situation, however after two friends recently expressed interest in moving in, I was thinking of "house hacking" and renting two of the rooms to them to offset some the mortgage.

Are you looking to create financial freedom on investing, or is this just a supplement to a holistic retirement strategy?