If you are a control person, this can be a challenge but I have learned to let go over day to day issues that come up that I would do differently.Handypersons are a tough one.

Any person over 18 should go through the tenant screening if they are living there...they don't necessarily need to be on the lease, but there is another area on the Chicago Association of Realtor's lease to add occupants.

(You can find the zoning map online.) 

I am seeing quotes around $120k which would put that cost per square foot around $600 which seems a lot compared to what I have seen/read online The reason your cost per square foot is so high is you still have to add all the things a regular house has but in a smaller space.

Full background checks.IDs, names of all people to occupy house.All move in money received, no personal checkslease signed by All.Walk through inspection completed and signed.

3) It's been 5+ years since we've seen a S8 tenant lose their voucher for property damages, not paying their portion of the rent or utilities, or other lease violations (letting others move in with them).It's our opinion that #2 & #3 above are caused by overworked caseworkers not having the time to process the extra required paperwork, so they take the path of least resistance.4) S8 needs someone at the federal level to put more of the program online and streamline the process!

Currently I manage personal rental property here in Canada.

Perhaps....but   the person relocating to any given market and who has to make a purchase in a finite period of time is generally the least likely candidate to get a great deal on the purchase, meaning the appreciation is even more important. 

@Kainoa Oneha Education is 100% back, whether in person or online.  

On the other hand, this phrase is often used by the likes of Uncle G (who, having an accounting degree, should really know better) to suggest claiming personal expenses as business deductions.