So, yes it is done all the time:)Would recommend requiring videos of work progress & completion, find your own 3rd party inspector to check on the work and if the project size warrants it, be prepared to fly out and personally inspect work.

Just before that, you should hire an inspector to identify what repairs are needed and add that to your improvements on the scope of work.

Lol....Indianapolis is great.

Property inspectors can usually give you a ballpark estimate for life left on a roof. 

Attorneys, Home Inspectors and Real Estate Agents please give me some advice!

I might also recommend finding a property inspector that is in (or at least familiar) with the rehab / flip industry to walk you through your first few properties.  

What the hell does this have to do with investing in Indianapolis?

By that time I had built up a team, had an inspector, and this property came out good.

The home inspector did not raise it as something that must be fixed, and it seems to have worsened since that time.

I had a trusted homes inspector that did pretty well.