Similar to @Ben Leybovich, my ability to maintain my W2 status long-term is jeopardized through a health concern.

But, I am an appraiser.Oh, and an appraiser should look at public records as a guide, but not the end all in the status of the property.

What's the current tenant status?

Having a builder's mind, I would always suggest that the buyer call the local city Building Dept and ask for permit status.

Taxes - with this model I wouldn't be able to move the property to an LLC (I would lose homestead status which is what is used to make the "owner-occcupied" determination).

This is very good advice to flippers to 1) file as S corp status on your LLC and 2) contribute to a retirement plan to offset a lot of your profits from flipping.

Our research is focused on the status quo of breaking a lease. 

More often than not, we buy run down properties and fully renovate them to relatively maintenance free status.

The main areas I am wanting to organize are my existing leads and their statuses of importance, where are my deals under contract in the process and what tasks need to be completed, and overall bookkeeping for income and expenses.

That's helpful to keep in mind with the 50 mile radius, as that applies to tax residence status for travel nursing.