I notice a lot of large apartment buildings in my area (Toronto) are being managed by third party property management companies.

No politician in their right mind would sign their name to such a thing, it would be ending their political career and forever tarnishing whatever political party that person belongs to.

Little late to the party here But I highly recommend @Mark Fries as well.  

I question the cashflow part. I

Nice part is, even if we have a hard time selling because it's section 8, it cash flows pretty well. 

If there is an option to upgrade and notably increase ROI, sure I'll consider that option, but for the most part, I want properties to be good to go with a little clean up.

I posted the property for rent on my personal social media that afternoon and had 5 interested parties, 2 of which are serious, both work in healthcare.

The funding part is probably the most confusing and nerve-racking part for me (and probably for most beginners). 

However, if you need anonymity and use a nominee or other obfuscation methods, you may not be able to do it yourself as you may have to use a third party.

The listing agent has a fiduciary responsibility to the seller, but also a responsibility to be honest to all parties in the transaction.