Also we are aging and not feeling great physically working on houses.

Obviously, ESA letter (if legitimate) gets them around the dog age, but what about spaying/neutering? 

@Kaias BlancoI will share with you some advice I got when I was about your age… maybe a few years older… I’m now 54… and this advice has served me well through the years; and it sounds so simplistic:   “You are where you are because you choose to be there.”What that means is that the limits as you currently see them are self imposed.  

Do a comp analysis to see what the market picked up and at what price, of apartment same type/age in the area.

It's best to delead when the units are vacant to avoid extra costs like hotel fees.In the case of a property transfer where a child under the age of six will reside in the property, the new owner is responsible for bringing the property into compliance on or before 90 days of the transfer of ownership.

Has anyone experienced this in the cook county area?
My insurance company stated they will not be renewing my property insurance policy due to my flat roof. I've had them for a year, and with in that year the company...

Also, when the minor child reaches the age of majority, asdefined by the law of the State or Indian tribe in which the reporting company was created orfirst registered, the exception no longer applies.

What other aspects should I keep in mind and look out for in a property of this age and condition?

@James McGovernA D Class property is based on age, and location.

Congrats for getting started at age 21 and I really wish you a lot of success, but I have bought my first rental property in Milwaukee 15 years ago and frankly, the market was much easier back then, I did not have the expense of a PM and cash flow was solid at about $200, but not amazing.