So I guess that's more of what I'm hoping to find - someone who could sort of break the steps down for him (i.e. like you said, start with contracted 1099 and then move on to W2 employees), that way it hopefully doesn't seem so insurmountable to him. 

Not saying this is an insurmountable obstacle!

The more I learn the more insurmountable this all seems.

@Eli JacksonThe best sound advice I can give you on getting started is to cool your jets a bit and get $25K on the side that you could put in a little pile on the sidewalk, douse it in gasoline, light it up, and still be all right with your finances and your family.While you're busy getting your money straight you can learn more about real estate investing, make contacts, and refine your business plan.If saving $25K in 2-3 years is an insurmountable target for you and your family, real estate investing might not be the best of ideas for you.

None of these are insurmountable hurdles though, and the benefits can be huge.

We work as a team to assist them in surmounting the hurdle that prevents them for purchasing a home.

Maintenance is certainly a concern, but I don't think it's insurmountable.  

I'm pretty sure the tenants with the rats will not be renewing because they think they have an insurmountable problem or something.

Generally, what's good for the goose is good for the gander.If executed properly, I see this being a big help to the worst RE markets with insurmountable inventory.

There will be challenges you will have to overcome but they will not be insurmountable.