So I always urge people to start with the end in mind and take a more passive approach.Do the math here… you with 300 dollars per property (2 months of work to buy a turnkey rental) you are going to need 20-40 of these to replace your income.

Another way to think about this is in terms of what kind of annual return you're going to need.

At some point I'm going to need to take the boards off and do the exterior/show the property.

@Eric Swope There is an underlying tone in most of the discussions involving contractors that they are out there to rip you off .  

It is a side by side duplex with a ancillary unit (converted garage into a single family) and after running through it with my home inspector and contractor, it's looking like I'm going to need to put $40k into it in just safety upgrades (3 unfit falling over porches, deteriorated window sills, smoke alarms, second means of egress).

At some point you're going to need help (contractor, realtor, PM, etc.) to reach your goals. 

You're going to need 20 - 25% down and I recommend a reserve to handle emergencies for that first year until you build up a reserve.

People are always going to need a place to stay.

For financing you are going to need to bring more to the table when working with a HML or using a commercial loan.

I just put four houses under contract and all of them are going to need extensive rehab work.