As I see it I'm betting on the housing market, rental market, YoY tax increases, and insurance companies.

Who does these (not looking for specific companies), is it accountants, lawyers, agents, and/or contractors? 

I'm on the lookout for investor-friendly title companies and lawyers.

Again, less than 10% of Americans go FSBO - and I don't think it's because they're lazy.Yes I'm a realtor so I'm showing a bit of my own bias.....but every year I've also given advice and helped homeowners who wish to sell their homes by themselves.

It'll be interesting to see if any other, more seasoned Canadian (or American) investors weigh in here on this topic.

Also, have an attorney and/or work with a title company to help you draft up the paperwork and close the deal. 

If it's a trust naming a person that has passed away, there is a person that is named on the trust to perform this for the person, or lawyer.A lawyer, or escrow company can give you more insight on the forms that are needed for this type of transaction and how to get them signed and processed.Good luck.

My property management company is willing to handle and manage the repairs (but since it'll be expensive I will likely want to go there so I can manage some of the repairs and pick out my materials).Out of the 3 options, this would come with the least amount of tax repercussions.Cons: Moderate stress.

If you have full time property management, it is hard to say you were the one doing "more then anyone else" since the management company is taking care of everything.

Nashville, TN is having some major companies like Alliance Bernstein have moved into Nashville, bringing the population up and new jobs into Music city as well.