I manage 8-12 unit buildings in Logan Square, Albany Parka and Irving Park, and we have had issues with porches even at that small sample size.  

Sadly, many of them don't have younger relatives to provide them guidance and many times are scammed by predatory investors.   

I feel like a lot of people work property management up to be a super time consuming thing, but with the right tenant in place, the right team on the ground and some software to manage things, it can be done from a far relatively easy. 

Specifically looking for a cross-border accountant, and legal counsel to ensure I get the right paperwork sorted to minimize double taxation, and related cross-border issues.Any other Canadian investors have experience with this, or accountants here who specialize in supporting with this?

., sold in the last year, relatively nearby, similar in size, etc.).

Is this too many issues to even considering buying? 

Obtaining competent management was an issue, I have no confidence in the service personal in the local area.  

Courts have ruled inconsistently on these issues. 

I have had to evict one guy for non payment of rent and evicting a woman on Tues for non payment of rent and disturbing the peace with her mental issues.

Yes, as long as it relates to the renting of the property in some fashion.