Something can come up and eat into your cash flow.

I don't want to eat that right at the start though.

So, if the foundation is bad and causes expenses to eat into your profit margin, I would pass.

She starts eating out at restaurants more often to enjoy her money.

If you can find someone to move in Aug 1, great, if not it is going to eat into their first month until you can find someone to move in. 

If we eat healthy every day, the weight will come off. 

You can save by removing mortgage insurance, but you'll pay more for the higher rate and possibly eat up any savings.

Painting after 5 years seems like something you are going to have to eat for the paint itself but you can charge what was allocated to the paint job to repair the holes and charge the tenant for that.  

So if it's at $100,000, and he accepts an offer at $60,000, he would be out on $40,000 in support.He is currently eating the fact that he has to upkeep the property while at the same time pay for the property taxes.

If you do get in though this could generate a few hundred each month but keep in mind these rentals don't always rent and get occupied same day so a month of holding costs may eat up a large part of your profits.