If you don't have in house management at your brokerage, there are third party managers here in town that would be happy to act as a resource for you, with the hope that you would occasionally refer clients their way.

I really enjoy visiting Destin, FL and staying in a beach front Condo occasionally, and I have always wanted to own one and rent it out while I'm not present so the unit pays for itself.

As an agent I do come across an occasional interested party.

I use one occasionally, but I also used to be one, so I self-help in that arena probably more than I should.2.

I have 4 drain spots on the building (all four corners) and the rain occasionally doesn't enter the drain spots and goes into the units.  

Sadly, in this business you will occasionally run into people who don't want to get sick or die and will instead do what is best for them and their staff instead of you. 

I am not sure about Canadian lending, but in the US there are occasionally forms the lender wants you to sign stating that you are not borrowing your downpayment. 

Do the numbers still work if your budget bloats by 30-50%?

Occasionally, I get to work on some CRE deals, but spend the majority of my time in the corporate space. 

Only one person but as an active investor who regularly surfs Zillow for background and occasional inquiries I can tell you the only call I ever make are to the listing agent.