It also kills two birds with one stone: an investment property, and a roof over your head. 

It takes some serious knowledge and work.I would not buy into an SA wine business without getting boots on the ground and doing some due diligence.

Needs more cosmetic work than major rehab, and roof was recently replaced.

Then roof starts falling. 

You have the mortgage, taxes, insurance, maintenance, capital expenditures (roof, flooring, etc.), and also need to consider the cost of vacancies or bad tenants.I also recommend you charge market rate, for yourself and the tenant.

I recommend establishing a reserve fund for major turnover expenses, capital repairs like a roof replacement, etc.

Has anyone been through the boots on the ground program with Brian Grimes?

Its already long distance but if you have no desire to be involved, no boots on the ground in anyway, it may be hard to make it work.

Electrical work, plumbing, foundation, windows, roofing, and AC/Heat.

And if all houses have not been fully rehabbed (we do fulls on every buy), some expected number for capital expenses should be included in that (IE if you have 3 years left on your roof you need to be deducting $X from that figure, repeat ad nauseum for all major capex).