We work with a lot of OOS investors and showings, inspections, and lending can all be done remote very easily. 

My goal was to just take his month late payments and give him a non-renewal when his lease is up.

What you owe doesn’t matter at all. 

Quote from @Donald Aleshire: Thanks for all the detailed feedback all!

Hi Allen, there are plenty of hard money/private money lenders here on BP, just take your time and speak with several of them to understand all the fees and requirements.

Therefore, working with a single real estate agent doesn't make much sense as it will limit you to his/her very limited inventory and he/she might have as main objective to sell a property to you take advantage of your lack of knowledge of the market.

Cash out would take me from a 7.25% rate to 8%, which is a few hundred dollars per month, and they will likely make me wait all through March to do the cash out to meet seasoning which is another $2400 interest payment I could avoid if we could refi by the end of this month.

I recommend you educate yourself on how to screen an ESA before someone takes advantage of your ignorance.

Do you pay all of it, some of it, etc?

That is not uncommon on all home owners policies.