I plan on hiring a general contractor ( like many do) and then hiring my property manager to manage him. 

Have you thought through all of that or are you still forming a plan? 

A guy with some discipline, ambition and planning is going to make a great living going forward.

It sounds like you may benefit from a 12 month bank statement program.

Planning to put more then 20% Downpayment .

Nick,Depending on what you have for a down payment there are other programs to help avoid the hourly and overtime. 

Our plan is to start this as a side business (we all have day jobs) and play the long game until we can eventually switch careers entirely.Books I've read recently:1) How to Invest in Real Estate, Brandon Turner2) Rich Dad Poor Dad, Robert Kiyosaki3) The Richest Man in Babylon, George ClasonMy goal is to eliminate as much ignorance on this topic as possible.

The plan for that is either rent out my room or convert it to a sober living facility.

It may not be how you planned it, but you won't regret it.

But I plan on adding a 40/60 split on the next lease renewal between the two units.