2) Employment - The current unemployment rate is meaningless without also including the participation rate.

Before you quit your W2, you'll want to make sure your rentals are making enough on paper to replace that other income.Once you quit your W2 job, you'll officially be considered self employed by lenders and the important thing to keep in mind is that we can only count your NET income.My advice is chat with a CPA who can help you structure your income properly and try and do it 2 years prior to quitting your W2 job.

As far as hitting the 2 year mark for your job, that might not be necessary as long as you have at least 2 years of employment history in general.

Yes can definitely turn your current primary into a rental and purchase a primary in FL where your employment is moving you to .

Based on the employment records the jobs thst afford them the apartment are new.

Alongisde that, it will be important to have stable employment, because your job is what helps you qualify.  

What tools or methods should I employ to evaluate its true market value?

With so many “alternative” qualifying programs out there, there really has to be something other than “under 2 years employed” or “doesn’t show all his income” for the buyer not to be able to obtain institutional financing, and hence be willing to spend $250k for a $200k house. 

@Mathew Morford what type of investing strategy are you planning on employing?

For example when a large employer in a small town closes up shop taxes may continue to go up at the same time as people move away or can't afford rent forcing rents downward.