My theory is as global warming drives people away from the coastlines (it is already driving insurance companies away), there will be a migration back to the Midwest where the weather isn't an extreme and prices are more reasonable.

Look at the Florida condo market to learn how the market can be affected by special assessments, weather-related disasters, insurance availability, as well as newly promulgated laws/regulations.

But of course, some (like your Lender) find it hard to resist slipping back into their pre-GFC ways!

I've been under the weather and couldn't get back sooner, but I appreciate all the guidance!

Maybe these questions can help get you where you want to be:What is going to make the process so smooth that he can't resist? 

Weather became a challenge, Portland had a huge ice storm in January when all my plumbing and electrical was going in.

Temperate weather, beautiful views and plenty of attractions; what else could you ask for!?  

High rents and not much weather on average.

Apparently with all the different weather related issues going on, and uptick in claims, some of the insurance carriers are no longer writing  Landlord policies in Oklahoma. 

The guest said she was house hacking but only stayed there in the property 6 months out of the year and short term least it out the winter months to travel and stay where it is warmer weather.