@Benjamin ShawIt sounds like you need to talk to a structural engineer to see if it's feasible to save. 

I'll definitely be looking to make some connections in the Real Estate profession, while avoiding the loss in time and expertise in my own profession.Your response is much appreciated!

This can be for things such as actual vacancy, bad debt, collection losses.

I'm having a difficult time calculating tax gain/loss from a property sale and was wondering if someone could help me with calculations.Purchased Home in 2005 for $145500Converted personal home to a rental property in 2008.

I guess we are basically trying to justify turning our cash-flowing rental into a second home. lol and the thought of selling a few homes a year there could help compensate for the loss in rental income. 

The main question we have is how feasible is it to pull our money back out in a refinance?

Besides liability you are insuring the property itself for somewhere between the loan amount and the market value (some companies are more flexible than others on requiring a minimum per sq foot or % of their view of replacement cost) in order to make the lender whole and protect your equity in the event of a total loss.  

(we would be open to any creative ownership structure that would allow this type of arrangement). 2) Provided #1 isn't feasible, could he use a 1031 exchange to buy another rental property with him and I acting as co-owners through an LLC?

This is more art than science but you could calculate what you need to have a 6-12 month emergency fund should the unexpected happen (job loss, economic crash, etc.) and keep that amount liquid or available.  

I want to get a Market feasibility study done to make sure the market is not over saturated.