However, the guy is a professional and has assets, furthermore his wife has hung pictures all over the house, I don't think he really wants to leave.

No pictures of the inside are available and no walkthroughs or inspections are permitted as it is occupied and being sold "as is".

My post wasn't so much about the obvious things to look for, those are covered everywhere, and I don't mind digging for those things as needed.

@Michael KistnerMake sure that your rental income covers your basis and you can support your living situation with the job.

I found a property manager to list the property which included pictures, listing, showings, tenant application and walk through.

The properties I am looking at will cash flow a teeny bit, enough to cover mortgage, interest, insurance, and 20-30% for repairs and vacancy.

Make your pictures bright and attractive.

This is specific to single family homes, so you could definitely lower these amounts, especially CapEx, for a condo where most of the major expenses will be covered by your HOA.  

I will be down there for closing to do some basic work and then back down there once the contractor completes the rehab we are doing, at which point I could take pictures and list the property on postlets.

And his rent covered my mortgage with just a little left over each month.