According to data I've read, home prices in the Orlando-Kissimmee-Sanford metropolitan area have gone up 12% annualized during this period. 60.9 - 12 = 48.9%.Does this mean that my rehab improvements improved the value of the home by 48.9%?

You separate the holding company for a number of reasons: rental income is taxed at a some of the lowest rates, and the risk of loss is different in character than that of running operations, its tax filing looks different (as a business) than a business that runs operations (deducting capital improvements, etc.), among others. 

Portfolio lenders typically follow the same (75%-80%) rule and consider the additional income from your properties and perhaps relax on the debt to income ratio and as long as the deal makes sense and generates positive cash flow.  

If not is there a rule of thumb people take after on the first after (5% or 10% below list price for example)?

Any advice on how to creatively and legally get around this 2 year rule would be greatly appreciated.       

The IRS rules allow me to manage it, but I have always used a property manager and will continue to do so.

What rules of thumb do you use for your preliminary "deal or no deal" analysis of a property?

At the same time, you can be improving your personal finance position to have a solid foundation for investing and taking calculated risks. 

Mine are closer to the 50% rule, so I'm playing it conservative.  

They also have there own set of rules for processing redemptions, etc. and you may or may not know, OK City n Tulsa just completed their sale.