In Chicago buildings this age it's normal/expected to have some settling.

My husband and I identified at an early age that becoming home owners was a non-negotiable life goal for us and purchased our first home at 21 yrs old. 

SEC 8 compares your requested rent to non-SEC8 properties of the same bedroom size, same property type, similar size and age, same city, within 5 miles.

I’m currently working landscape and construction, making decent money for my age but I want more.

Basements are the issue specifically not necessarily the age per se.. basements leak !! 

-I'd like to retire in 12 years (at the age of 52)Scenarios I've played with in spreadsheets:-Highest long-run returns - Investing it all in syndication deals.

I have had an interest in real estate from a young age.

I would love to be able to retire at age 50 or 55 and I think investing in real estate could be the way to get there. 

Their lease ends on 8/31, and they have the option to resign or become TAW.The problem comes in because I am moving since life (career changes and aging parent).

Last month, his daughter, son-in-law, and their five kids aged approx. 12-1 yr old moved in from out of state temporarily while they look for a more permanent place.The lease prohibits guests for more than 30 days without my permission.