But I can do it forever, so there has to be a plan bring them up to market value or have an exit plan that doesn't put them in an even tougher situation a year from now.

With interest rates getting weird and insurance tougher to engage, this is a must-have protection).I recommend checking on insurance upfront too.

When you talk about renting a larger home You are right, it can be tougher.

I don't expect too much appreciation but the house is clean and I figured 10% vacancy rate to account for the tougher market there.

Condos can be a bit tougher.

Rick H. is exactly correct, and, after 20-years in banking, I would say Wells is one of the tougher banks to deal with. 

my general thought is that when you hear of success stories in the 30 to 40k sfr rental properties it is generally those that live and work in the market that can make them work out of area investors have a much tougher time as the tenant demographic that rents those homes is a management intensive group by and large.You may want to look at buying more of a 4 plex type of situation were you can get a FHA loan and now you have 4 doors instead of one and you don't burn through your 10 loans one door at a time. if you bought 10 4 plexs you would have 40 doors with the same credit.

Chicago has neighborhoods full of condos where very few people (if any) over 40 live.The "popular" places in Chicago are excellent for young professionals until they have kids, then it becomes tougher to justify staying there and most move to the suburbs or a quitter area of the city/

If not, you are in a much tougher situation.

It is my understanding the laws have gotten even tougher on getting unpaid child support.