When I'm driving and see a property I may be interested in learning more about, I text myself the address or a picture.

Let's look at your example of a roofer, assuming he owns the company.He has to pay for employees- they still get paid, even if they are not giving 100% effort.He has to pay his workers to go back for warranty work - effectively paying them to do the same job twice.He has to pay for equipment, even when it's not being used 100% of the time.- but the company he bought it from still gets paid.He has to pay for advertising, whether it works or not.- but the advertising company still gets paid.He has to pay for accounting services, payroll services, tax services, legal services, etc.- they all get paid whether he makes money or not.So, what's your point?

As the new owner, you’ll want the lease and your landlord insurance policy to take effect as soon as you take title to the property.Temporary Lease Considerations:While short-term leases can work well, leasing to a seller long-term often leads to complications.

We have also addressed where we fell short and failed to follow through. 

He offers really good service, great cost effectiveness, and currently finished one in just around 3 months. 

I'm going to reiterate what's already been mentioned above, but I'm going to actually give you examples of why it's relevant to you to find a U.S. tax professional.1 - You're going to need to file U.S. taxes once you have property down here, there's federal filings, state filings, and sometimes local filings too2 - Tons of tax treaties between the U.S. and Canada that are easy to miss and can cost you a lot of money (important one with rentals - effectively connected income - if the professional you talk to doesn't know what this is, run away)3 - The amount of days you spend in the U.S. needs to be tracked and if you go over a threshold, all of your worldwide income could be taxable by the U.S.4 - Selling real property means up to 15% of your sales proceeds might not be available to you for years (FIRPTA)5 - Lots of nuance at the state and local levels, which both want to take as much money from you as possibleMain takeaway here is that you should find a U.S. based tax person.

By house hacking, you're immediately positioned as a landlord, which will adequately pressure you to learn how to structure your leases, screen applications, collect rental payments, resolve the nuances of managing tenants and addressing property issues, etc.

However, the MLS in San Diego as well as the appraisers I've worked with do.You'll definitely want to check to see how the topic is addressed in the particular locale the property is in. 

There are many problems with the concept which you have not bothered to address. 

RISKSPrivate Letter Rulings There are three (3) Private Letter Rulings (“PLRs”) that address this 1031 Exchange structure, which are as follows: Private Letter Ruling Number 2014-08019Private Letter Ruling Number 2003-29021Private Letter Ruling Number 2002-51008PLRs can only be relied upon by the individual taxpayers that requested the PLRs.