We both do plenty of on our own things, but he'll send me something to fund and he'll manage the 'boots on the ground' aspect.

Sounds like they did a bare minimum cosmetic rehab and ignored all the important aspects of the property to save money.

Roof...

I just rented out my first investment property but still need to do work in the garage (roof, door, tree cutting).

Critics of this method sometimes struggle with this aspect but when you consider it along with the other theories it makes perfect sense.

The biggest things you want to look at in the inspection report are the roof, foundation, and moving pieces (hot water heater, HVAC, plumbing system, and appliances. 

Hi Folks,Any idea on if insurance would cover a roof that I repair myself.

So, that $2000 new roof, don't go for it!

What type of roof? 

start by driving around areas in your town you would want to invest. find houses that look like they need work (bad roof, bad siding, long grass, etc) and look them up on the tax assessor website. try to get in touch with them (facebook, google, etc) and see if they want to sell. research rents and comps in the area and make sure your purchase price and after repair value will work as a cash flowing property. this is the cheapest and easiest way to start.