This is the first home that I am landlording and the first tenant was amazing, I was sad to see her leave but happy because of the reason she left was a good one.I am looking for advice from you seasoned pros! 

From the financing side of things - keep in mind that conventional cash out refinances require 12 months of seasoning in order to use the new appraised value.

I would check this out with a seasoned securities attorney for their opinion/guidance.  

They recently renewed their lease, and it was in my intention to ask for the new renters insurance, and things got busy during the holiday season and I never took the time to ask them.

If it does sooner than later, or really at any point, it means destruction in the economy and if you were waiting you are probably impacted by this destruction.Rates moderate and season here for some time with opex being a persistent headwind.

We want to see equity, seasoning, a quality borrower, and good terms. 

I don't know your specific market all that well but have you done some analysis on your ADR during the high season X your high season occupancy rate and determined whether taking lower priced slow season bookings vs letting your property stay vacant during the winter averages out in your favor?

Also, how do you factor or account for an area/town that experiences lots of seasonal tourism, compared to the town that does not? 

I'd say each property on average has at least 2 bookings a week ( more during the on season) so that's about 34 hours a week average.

Some are led by seasoned investors with a wealth of knowledge, while others may be run by people with minimal experience.