Also as a HML ( which I have been) I would not do a deal that is one off in an area were I don't have a concentration of loans if it went bad its too expensive to travel there and try to figure it all out.. kind of like a white elephant loan.

@Simond Wong  I try to maintain part of my portfolio to be section for the guaranteed income and long term tenants.

It does not seem the same as the case of a promoter offering a guaranteed passive investment and maintaining title to the note the whole time.

Being A/D military it is a bit tough to maintain homes when we move every 2 years but we are up for the challenge and look forward to learning from all of you!

—In all criminal cases, contempt cases, and other cases filed pursuant to this chapter, if a party has sold, leased, or let real estate, the title to which was not in the party when it was offered for sale, lease, or letting, or such party has maintained an office bearing signs that real estate is for sale, lease, or rental thereat, or has advertised real estate for sale, lease, or rental, generally, or describing property, the title to which was not in such party at the time, it shall be a presumption that such party was acting or attempting to act as a real estate broker, and the burden of proof shall be upon him or her to show that he or she was not acting or attempting to act as a broker or sales associate.

We are looking to get another property or two this year while maintaining our full time jobs.The problem is where!? 

She lives here in New York, is a mother to three children, and her and her husband are concentrating on purchasing a new home for their family here.Ten years ago, our father encouraged her to buy this land but never pressed her to do something with it.

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!