By limiting the amount of money the free market would let flow to a property owner, the government is in turn limiting how much money that property owner can then spend to maintain their property.  

In this way, you don't need to depend on just your W2 income to qualify for more mortgages.More mortgages are not necessarily riskier, as long as you maintain an equity cushion and positive cash flow (with margin) on each property.

The 20% put up by you would go into a reserve account maintained by the lender and would pay no interest while being held.

Augustine has a lot of different neighborhoods...beautiful beaches...Intracostal...high dollar golf communities...quaint historic area...older neighborhoods with concrete block homes with big lots being being brought back to mid century style...less desirable neighborhoods that may never be...you need to decide what niche you want to concentrate on...I think you tell which I like....but a lot of buyers and investors have discovered our beautiful slice of paradise and potential deals are difficult to come by...

The way you propose to do this (with great comments from @Daniel Chang as well) by switching over to the new rent, rentable square footage, and operating expense schedules while maintaining the tenants same initial bottom $$ line is a great strategy, will likely not illicit any objection, and set the very important foundation for your office investment to profit and grow in the future. 

And thanks for your vision and hard work in creating and maintaining a great educational REI site, along with the awesome podcasts! 

Now I'm not a licensed agent but I do have quite a few anecdotes about how agents and others that work in the industry here put up huge roadblocks to maintain the status quo.

We sold all of our prior holdings in 2006 to concentrate on another business. 

Once you set up each entity, it is fairly easy to maintain.  

Look at how the properties are maintained; what types of vehicles are in the driveways/carports, etc.