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I find it easier to do comps. 

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@Guy AztaYou need to get rid of the property management company, which is easier said than done.

It appears that I can refinance (no cash out) to an interest rate of 4.8% however with the remaining balance on the mortgage that I would be borrowing my total payment will drop to $1,787.00 per month and I will no longer have PMI. 

I think when you have one deal behind you it'll get easier.

It is also easier to just pull out a credit card instead of having to deal with cash...I know some will argue that this ease of use is dangerous due to the potential to spend money that i don't actually have...but rest assured, my social awkwardness far outweighs my urge to spend money when I do make it out of the house.  

It would be easier if I asked them for contact information when they sign the lease or any time they sign a renewal.

It would be easier to add more coverage right? 

I am wondering what advice you all might have, as properties in Florida higher, so should we look up north for a property that might be a bit easier for us to finance.