As you and many others have mentioned it seems to be a large risk and I am trying to do everything I can to limit that risk, but at the end of the day a bad HOA is a deal breaker for me.

If there is only one, it's a common system that the owner pays for.This isn't necessarily a deal breaker.

An outlet in the house burnt out ( I am thinking it is due to them)  but they had to shut the breaker off which shut the power off to some bedrooms in the house.I scheduled a electrician to come out the following day but the tenant texted me saying they cant be there to meet him.  

i would put in smoke detectors, handrails and lighting, i also believe that because it is a multifamily that is a requirement that even the town has. if you are referring to electrical outlets and separating circuits, then yes, when you remodel that triggers bringing everything up to code.

You may want to see if the parking area (if there is one) is heated - this can be a real deal breaker for Chicago weather.

That means that even though your cable company may advertise 30, 50 or 100 mbs, you might not get any where near those speeds it is dependant on how many other households share the same circuit and how much they use the circuit.

I am very handy and will try to salvage the breaker panels from the building I'm tearing down. 

If you want a tie-breaker,  you can hire a structural engineer for around $400 - they will give you a clear statement as to what is needed.Also, be sure to consider the age of the house and where you are lifting e.g. near a bath, kitchen or other potential drain line) - if it is an older house and has cast iron pipes, you will probably have some plumbing work when you are done lifting. 

I don't rent to anyone who fails these standards - felons, evictees, not enough income, and a credit score under 600 is probably a deal-breaker as well.

Breaker box needed to be updated.