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

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. 

We would like to do it all legally with plans approved by the town.Any recommendations for an architect / company that can assist us with this project? 

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.  

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

Networking with local investors can provide valuable referrals to reputable contractors.

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".

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

I am curious as well and will be following this thread - I use Quickbooks because we also have a construction company and it works well for that BUT I have to email an invoice to each tenant every month with a link to pay online.