The only thing I would anticipate needing in terms of capital expenses in the next few years would be a new HVAC unit which is on the older side, but we have already budgeted for that and have a service contract with a company that manages our HVAC, water heater and oil tank.Am I crazy for thinking that a property management company would be an unnecessary expense in my case?

FHA has caught on to this trend & updated the guidelines to prevent people from abusing FHA financing.Here are the guidelines directly from the FHA Handbook:Policy Exceptions Eligibility RequirementsRelocation: A Borrower may be eligible to obtain another FHA insured Mortgage without being required to sell an existing Property covered by an FHA-insured Mortgage if the Borrower is: • relocating or has relocated for an employment related reason; and • establishing or has established a new Principal Residence in an area more than 100 miles from the Borrower’s current Principal Residence.

Designed to prevent the ground from shifting.

It prevents people from "sniping" other people's recruits and keeps things on the up and up. 

In fact  there's a company that markets quite heavily on this BP that sells uneducated investors formation packages that are completely impractical and unnecessary but there are plenty of accountants out there who do the same.  

But what is to prevent a tenant from later claiming that they had made a timely - verbal - demand for their security deposit?

This changes with a few factors but it works to prevent issues in buying the wrong property.

This would help prevent canceling any bookings and losing them when asking to re-book.Has anyone done this? 

This means rental income, dividends, and capital gains from U.S. investments must be reported on your Canadian tax return.Foreign Tax Credit: The good news is that Canada has a tax treaty with the U.S. to prevent double taxation.

Hey Mik, I have a condo as well and have thought about converting it into a MTR or STR but the restrictions by the condo association completely prevent this.