A great PMC (Property Management Company).Whatever rental you buy, they have to deal with it every day. 

Similar to if you hired a company to replace a roof-you don't have a copy of the bill for all of the shingles and nails, but you have a copy of their bill that has those effectively built in.

The agent told me that Tower Hill (the insurance company) can’t adjust the occupancy status and that I’d have to rewrite a new policy for occupancy.

A lot of people don’t realize this, but in addition to real estate agents selling stuff, they are also being sold, every brokerage, every title company, even lenders, have courses on literally scripts, how to build out your social media, how to find fsbo listings etc, truth is none of these are effective, pretty much the only way to be a successful agent is either ton of ad spend or the hard work of meeting people in person through events meetups etc, but brokerages make money by head count, even title and lenders are happy if you close a few deals a year with them, so they sell this stuff to agents who than use those scripts on you, it’s a whole prymond scheme lol

Talk to an (investor savvy) agent or STR management company while you are there. 

My company has done 1031s for 31 years, we work in all 50 states, and we're very good at what we do. 

I have started a property management LLC company to manage these properties for myself and hope to grow that business as well. 

Although a bank or insurance company would fit nicely into Berkshire’s existing platform, Canada does have restrictions on foreign ownership of those assets – so my bet would be either an energy or utility-oriented opportunity (plenty of them in Alberta) or perhaps a significant stake in Alimentation Couche-Tard, which owns the Circle K brand and has a significant global presence, potentially meshing nicely with Berkshire’s recent purchase of Pilot Flying J.This year, I had the pleasure of travelling to Omaha with some friends from New York University’s Real Estate Development program and got to catch up with old friends from all over the world.Alas, my favorite Buffett-ism from the meeting was "Understand that the market is there to serve you, not instruct you".

Hi, I'm in the process of starting a vacation rental management company (already have clients ready to signup) and would love feedback from other property managers on best management software to use.  

The advice, negotiation, referrals to inspectors, lenders, contractors, lawyers, title companies, etc.