His hint was that it is the responsibility of the contractor and PM to make sure it is secured as they knew I was not in town on a regular basis.  

Properties meeting at least one of the following criteria will not be eligible for Citizens Personal Residential Multiperil coverage:Rented to guests more than three times in a calendar year for periods of less than 30 days or one calendar month, whichever is lessAdvertised or held out to the public as a place regularly rented to guests

Is there a regular schedule for the meet up?

I regularly attend workshops and seminars to stay updated on industry trends and best practices.

Yes, this strategy is an attempt to lower my wife’s taxable income.

Years ago, when I was in the retail leasing phase, I was regularly presented with this sort of nonsense and consistently refused to sign.

You don't have the benefit of maximizing cost segregation, long term capital gain, 1031 exchange, refinancing / lending, passive income vs regular income, etc.  3. 

Some reassess taxes when a property is sold, others do it yearly or every couple of years, regardless of sales.You can ask the county assessor how they handle reassessments and whether it’s tied to sales or a regular schedule.

Most issues will pop up in the first few months as guests use the place regularly, so have a good relationship with a handyman and maybe throw him some small jobs so that he will be on standby when needed.

They generally have large portfolios allowing for in house maintenance and management staff along with a point person who is communicating with the local housing authority on a regular basis and has the ability to streamline operations.