I can tell they are both on top of their game.

Then you hire a coach to accelerate your learning and take you to the next level.Using a sports analogy, it would be foolish to hire a basketball coach if your intent is to play pickup games every Saturday for fun.

There are mortgage recast calculators online or you can reach out to your lender.P+I payment will go from 2155 to ~1800 given the numbers you provided.

Was it via docusign or some other online signing platform? 

If the software is not simplifying your life or making you more accurate, you shouldn't use it.Software does have extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

This is my first personal mortgage so I'm trying to learn the game.

I offer an online payment portal to submit rent payments via ACH or CC - they "couldn't figure out how to use it" so I set us up to accept Zelle payments.

When it comes to a lifestyle property, it's another ball game and all the comments you wrote make total sense, especially for people who like similar things in life.

There are so many plays to run in this game I don't have time to type them all. 

My best advice to you, partner with someone who knows their market and has a solid game plan.